Herbicidal sulfinimidoyl- and sulfonimidoyl benzoyl derivatives

ABSTRACT

The invention relates to sulfmimidoyl- and sulfonimidoylbenzoyl derivatives of the general formula (I). In said formula (I), R, R′, X, W and Z represent radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogens. Q represents a cyclohexandionyl-, pyrazolyl-oder isoxazolyl radical.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a §371 National Stage Application of PCT/EP2013/053151, filed Feb. 18, 2013, which claims priority to EP 12156310.0, filed Feb. 21, 2012.

BACKGROUND

1. Field of the Invention

The invention relates to the technical field of the herbicides, in particular to that of the herbicides for the selective control of broad-leafed leaves and weed grasses in crops of useful plants.

2. Description of Related Art

WO 03/014071 A1 and WO 2011/012247 A1 disclose herbicidally active benzoylcyclohexanediones carrying an alkylsulfenyl, alkylsulfinyl or alkylsulfonyl group in the 3-position of the phenyl ring. Herbicidally active benzoylpyrazoles carrying an alkylsulfenyl, alkylsulfinyl or alkylsulfonyl group in the 3-position of the phenyl ring are known from WO 2008/125214 A1 and WO 2009/149806 A2. US 2011/0144345 A1 and WO 2004/052849 A1 each disclose benzoyl derivatives carrying a sulfoximino group in the 3-position of the phenyl ring. However, the herbicidal activity and/or the crop plant compatibility of the compounds mentioned in these publications is not always sufficient.

SUMMARY

It is an object of the present invention to provide herbicidally active compounds having improved properties compared to the compounds known from the prior art.

It has now been found that benzoyl derivatives carrying a sulfin- or sulfonimidoyl group in the 3-position of the phenyl ring are particularly suitable as herbicides.

Accordingly, the present invention provides sulfinimidoyl- and Sulfonimidoylbenzoyl derivatives of the formula (I) or salts thereof

in which the symbols and indices have the following meanings: Q is a radical Q1, Q2, Q3, Q4 or Q5,

R^(a) is hydroxyl, R⁶S, R⁷(R⁸)N, R^(b), R^(c), R^(f) and R^(e) independently of one another are each hydrogen or (C₁-C₄)-alkyl, R^(d), R^(e) independently of one another are each hydrogen or (C₁-C₄)-alkyl or together with the carbon atom to which they are attached form a carbonyl group, R^(h) is hydrogen, (C₁-C₆)-alkylsulfonyl, (C₁-C₄)-alkoxy-(C₁-C₆)-alkylsulfonyl, phenylsulfonyl, phiophenyl-2-sulfonyl, benzoyl, benzoyl-(C₁-C₆)-alkyl, benzyl, where the five last-mentioned radicals may optionally be mono- or polysubstituted by halogen, (C₁-C₄)-alkyl or (C₁-C₄)-alkoxy, R^(i) is (C₁-C₄)-alkyl, R^(k) is hydrogen, (C₁-C₄)-alkyl, (C₃-C₇)-cycloalkyl, A and Y independently of one another are each oxygen, S(O)_(n), N(R³), carbonyl or (C₁-C₄)-alkylene which is substituted by n radicals R⁹ and interrupted by n elements from the group consisting of oxygen, S(O)_(n), N(R³) and carbonyl, X is nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkenyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkenyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkenyl-(C₁-C₆)-alkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C, R¹(R¹O)N(O)C, (R¹)₂N(R¹)N(O)C, R¹(O)C(R¹)N(O)C, R²O(O)C(R¹)N(O)C, (R¹)₂N(O)C(R¹)N(O)C, R²(O)₂S(R¹)N(O)C, R¹O(O)₂S(R¹)N(O)C, (R¹)₂N(O)₂S(R¹)N(O)C, R¹O, R¹(O)CO, R²(O)₂SO, R²O(O)CO, (R¹)₂N(O)CO, (R¹)₂N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N, R¹O(O)₂S(R¹)N, (R¹)₂N(O)₂S(R¹)N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S, (R¹)₂N(O)C(R¹)N(O)₂S, (R⁵O)₂(O)P, R¹(O)C—(C₁-C₆)-alkyl, R¹O(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C—(C₁-C₆)-alkyl, (R¹O)(R¹)N(O)C—(C₁-C₆)-alkyl, (R¹)₂N(R¹)N(O)C—(C₁-C₆)-alkyl, R¹(O)C(R¹)N(O)C—(C₁-C₆)-alkyl, R²O(O)C(R¹)N(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N(O)C—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, R¹O(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, NC—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl, R¹(O)CO—(C₁-C₆)-alkyl, R²(O)₂SO—(C₁-C₆)-alkyl, R²O(O)CO—(C₁-C₆)-alkyl, (R¹)₂N(O)CO—(C₁-C₆)-alkyl, (R¹)₂N—(C₁-C₆)-alkyl, R¹(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N—(C₁-C₆)-alkyl, R²O(O)C(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N—(C₁-C₆)-alkyl, R¹O(O)₂S(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S(R¹)N—(C₁-C₆)-alkyl, R²(O)_(n)S—(C₁-C₆)-alkyl, R¹O(O)₂S—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S—(C₁-C₆)-alkyl, R¹(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, R²O(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, (R⁵O)₂(O)P—(C₁-C₆)-alkyl, phenyl, heteroaryl, heterocyclyl, phenyl-(C₁-C₆)-alkyl, heteroaryl-(C₁-C₆)-alkyl, heterocyclyl-(C₁-C₆)-alkyl, where the six last-mentioned radicals are each substituted by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups, Z is hydrogen, nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkenyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkenyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkenyl-(C₁-C₆)-alkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C, R¹(R¹O)N(O)C, (R¹)₂N(R¹)N(O)C, R¹(O)C(R¹)N(O)C, R²O(O)C(R¹)N(O)C, (R¹)₂N(O)C(R¹)N(O)C, R²(O)₂S(R¹)N(O)C, R¹O(O)₂S(R¹)N(O)C, (R¹)₂N(O)₂S(R¹)N(O)C, R¹O, R¹(O)CO, R²(O)₂SO, R²O(O)CO, (R¹)₂N(O)CO, (R¹)₂N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N, R¹O(O)₂S(R¹)N, (R¹)₂N(O)₂S(R¹)N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S, (R¹)₂N(O)C(R¹)N(O)₂S, (R⁵O)₂(O)P, R¹(O)C—(C₁-C₆)-alkyl, R¹O(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C—(C₁-C₆)-alkyl, (R¹O)(R¹)N(O)C—(C₁-C₆)-alkyl, (R¹)₂N(R¹)N(O)C—(C₁-C₆)-alkyl, R¹(O)C(R¹)N(O)C—(C₁-C₆)-alkyl, R²O(O)C(R¹)N(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N(O)C—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, R¹O(O)₂S(R^(1′))N(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, NC—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl, R¹(O)CO—(C₁-C₆)-alkyl, R²(O)₂SO—(C₁-C₆)-alkyl, R²O(O)CO—(C₁-C₆)-alkyl, (R¹)₂N(O)CO—(C₁-C₆)-alkyl, (R¹)₂N—(C₁-C₆)-alkyl, R¹(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N—(C₁-C₆)-alkyl, R²O(O)C(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N—(C₁-C₆)-alkyl, R¹O(O)₂S(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S(R¹)N—(C₁-C₆)-alkyl, R²(O)_(n)S—(C₁-C₆)-alkyl, R¹O(O)₂S—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S—(C₁-C₆)-alkyl, R¹(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, R^(2O)(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, (R⁵O)₂(O)P—(C₁-C₆)-alkyl, phenyl, heteroaryl, heterocyclyl, phenyl-(C₁-C₆)-alkyl, heteroaryl-(C₁-C₆)-alkyl, heterocyclyl-(C₁-C₆)-alkyl, where the six last-mentioned radicals are each substituted by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups, W is hydrogen, halogen, nitro, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₇)-cycloalkyl, halo-(C₃-C₇)-cycloalkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, (C₁-C₆)-alkyl-(O)_(n)S—, (C₁-C₆)-haloalkyl-(O)_(n)S—, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₄)-haloalkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N, R¹(O)C(R¹)N or R²(O)₂S(R¹)N, R is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, each of which is substituted by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (C₃-C₆)-cycloalkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C, R¹(R¹O)N(O)C, R²(O)₂S(R¹)N(O)C, R¹O(O)₂S(R¹)N(O)C, (R¹)₂N(O)₂S(R¹)N(O)C, R¹S(O)C, R¹O, R¹(O)CO, R²(O)₂SO, R²O(O)CO, (R¹)₂N(O)CO, (R¹)₂N, R¹O(R¹)N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N, R¹O(O)₂S(R¹)N, (R¹)₂N(O)₂S(R¹)N, R²(O)_(n)S, R¹C(O)S, R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S, (R¹)₂N(O)C(R¹)N(O)₂S and (R⁵O)₂(O)P, or is (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl, heteroaryl-(C₁-C₆)-alkyl, heterocyclyl, heterocyclyl-(C₁-C₆)-alkyl, phenyl-O—(C₁-C₆)-alkyl, heteroaryl-O—(C₁-C₆)-alkyl, heterocyclyl-O—(C₁-C₆)-alkyl, phenyl-N(R¹)—(C₁-C₆)-alkyl, heteroaryl-N(R¹)—(C₁-C₆)-alkyl, heterocyclyl-N(R¹)—(C₁-C₆)-alkyl, phenyl-S(O)_(n)—(C₁-C₆)-alkyl, heteroaryl-S(O)_(n)—(C₁-C₆)-alkyl or heterocyclyl-S(O)_(n)—(C₁-C₆)-alkyl, each of which is substituted in the cyclic moiety by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C, R¹(R¹O)N(O)C, R²(O)₂S(R¹)N(O)C, R¹O(O)₂S(R¹)N(O)C, (R¹)₂N(O)₂S(R¹)N(O)C, R¹S(O)C, R¹O, R¹(O)CO, R²(O)₂SO, R²O(O)CO, (R¹)₂N(O)CO, (R¹)₂N, R¹O(R¹)N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N, R¹O(O)₂S(R¹)N, (R¹)₂N(O)₂S(R¹)N, R²(O)_(n)S, R¹C(O)S, R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S, (R¹)₂N(O)C(R¹)N(O)₂S, (R⁵O)₂(O)P and R¹O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups, R′ is hydrogen, nitro, halogen, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-alkenyl, halo-(C₃-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R¹(O)C, R²O(O)C, (R¹)₂N(O)C, R²S(O)C, (R¹)₂N(S)C, R¹(R¹O)N(O)C, R²(O)₂S(R¹)N(O)C, (R¹)₂N(O)₂S(R^(1′))N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S, (R²)₃Si—(C₁-C₆)-alkyl-(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S, (R¹)₂N(O)C(R¹)N(O)₂S, R²(O)₂S(R¹)N(O)₂S, (R⁵O)₂(O)P, (R²)₃Si, R¹(O)C—(C₁-C₆)-alkyl, R¹O(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C—(C₁-C₆)-alkyl, (R¹O)(R¹)N(O)C—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, R¹O(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl, R¹(O)CO—(C₁-C₆)-alkyl, R²(O)₂SO—(C₁-C₆)-alkyl, R²O(O)CO—(C₁-C₆)-alkyl, (R¹)₂N(O)CO—(C₁-C₆)-alkyl, (R¹)₂N—(C₁-C₆)-alkyl, R¹(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N—(C₁-C₆)-alkyl, R²O(O)C(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N—(C₁-C₆)-alkyl, R¹O(O)₂S(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S(R¹)N—(C₁-C₆)-alkyl, R²(O)_(n)S—(C₁-C₆)-alkyl, R¹O(O)₂S—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S—(C₁-C₆)-alkyl, R¹ (O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, R²O(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, (R⁵O)₂(O)P—(C₁-C₆)-alkyl, (R²)₃Si—(C₁-C₆)-alkyl, phenyl, heteroaryl, heterocyclyl, phenyl-(C₁-C₆)-alkyl, heteroaryl-(C₁-C₆)-alkyl, heterocyclyl-(C₁-C₆)-alkyl, where the six above-mentioned phenyl, heteroaryl and heterocyclyl radicals are substituted in the cyclic moiety by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups, R¹ is hydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, cycloalkyl-(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl, heteroaryl-(C₁-C₆)-alkyl, heterocyclyl, heterocyclyl-(C₁-C₆)-alkyl, phenyl-O—(C₁-C₆)-alkyl, heteroaryl-O—(C₁-C₆)-alkyl, heterocyclyl-O—(C₁-C₆)-alkyl, phenyl-N(R³)—(C₁-C₆)-alkyl, heteroaryl-N(R³)—(C₁-C₆)-alkyl, heterocyclyl-N(R³)—(C₁-C₆)-alkyl, phenyl-S(O)_(n)—(C₁-C₆)-alkyl, heteroaryl-S(O)_(n)—(C₁-C₆)-alkyl, heterocyclyl-S(O)_(n)—(C₁-C₆)-alkyl, where the fifteen last-mentioned radicals are each substituted by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R³O(O)C, (R³)₂N(O)C, R³O, (R³)₂N, R⁴(O)_(n)S, R³O(O)₂S, (R³)₂N(O)₂S and R³O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups, R² is (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, cycloalkyl-(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl, heteroaryl-(C₁-C₆)-alkyl, heterocyclyl, heterocyclyl-(C₁-C₆)-alkyl, phenyl-O—(C₁-C₆)-alkyl, heteroaryl-O—(C₁-C₆)-alkyl, heterocyclyl-O—(C₁-C₆)-alkyl, phenyl-N(R³)—(C₁-C₆)-alkyl, heteroaryl-N(R³)—(C₁-C₆)-alkyl, heterocyclyl-N(R³)—(C₁-C₆)-alkyl, phenyl-S(O)_(n)—(C₁-C₆)-alkyl, heteroaryl-S(O)_(n)—(C₁-C₆)-alkyl, heterocyclyl-S(O)_(n)—(C₁-C₆)-alkyl, where the fifteen last-mentioned radicals are each substituted by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R³O(O)C, (R³)₂N(O)C, R³O, (R³)₂N, R⁴(O)_(n)S, R³O(O)₂S, (R³)₂N(O)₂S and R³O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups, R³ is hydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl or phenyl, R⁴ is (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl or phenyl, R⁵ is hydrogen or (C₁-C₄)-alkyl, R⁶ is (C₁-C₄)-alkyl or is phenyl which is substituted by m radicals from the group consisting of halogen, nitro, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy, R⁷ is hydrogen, (C₁-C₄)-alkyl or (C₁-C₄)-alkoxy, R⁸ is hydrogen or (C₁-C₄)-alkyl, or R⁷ and R⁸ together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated, partially saturated or unsaturated ring which additionally contained n heteroatoms from the group consisting of nitrogen, oxygen and sulfur and which is substituted by m radicals from the group consisting of halogen, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy, R⁹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy or (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, m is 0, 1, 2, 3, 4 or 5, n is 0, 1 or 2, s is 0, 1, 2 or 3, t is 0 or 1.

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

In formula (I) and all formulae given below, alkyl radicals which have more than two carbon atoms may be straight-chain or branched. Alkyl radicals are, for example, methyl, ethyl, n- or isopropyl, n-, iso-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Analogously, alkenyl is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methyl-but-3-en-1-yl and 1-methyl-but-2-en-1-yl. Alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl. In each case, the multiple bond may be located in any position of the unsaturated radical. Cycloalkyl is a carbocyclic saturated ring system having three to six carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Analogously, cycloalkenyl is a monocyclic alkenyl group having three to six carbon ring members, for example cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, where the double bond may be located in any position.

Halogen is fluorine, chlorine, bromine or iodine.

Heterocyclyl is a saturated, partially saturated or completely unsaturated cyclic radical which comprises 3 to 6 ring atoms, 1 to 4 of which are from the group consisting of oxygen, nitrogen and sulfur, and which may additionally be condensed with a benzo ring. Heterocyclyl is, for example, piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl and oxetanyl,

Heteroaryl is an aromatic cyclic radical which comprises 3 to 6 ring atoms, 1 to 4 of which are from the group consisting of oxygen, nitrogen and sulfur, and which may additionally be condensed with a benzo ring. Heteroaryl is, for example, benzimidazol-2-yl, furanyl, imidazolyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, thiophenyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl, 2H-1,2,3,4-tetrazolyl, 1H-1,2,3,4-tetrazolyl, 1,2,3,4-oxatriazolyl, 1,2,3,5-oxatriazolyl, 1,2,3,4-thiatriazolyl and 1,2,3,5-thiatriazolyl.

If a group is substituted by a plurality of radicals, this means that this group is substituted by one or more identical or different of the radicals mentioned. This applies analogously to the construction of ring systems from different atoms and elements. Here, compounds of which the skilled worker knows that they are chemically unstable under standard temperature and pressure conditions are excluded from the claims.

Depending on the nature and the attachment of the substituents, the compounds of the formula (I) may be present as stereoisomers. If, for example, one or more asymmetrically substituted carbon atoms are present, it is possible for enantiomers and diastereomers to occur. Stereoisomers also occur when n in the grouping S(O)_(n) n is 1 (sulfoxides). Moreover, the sulfur atom in the sulfoximino group or the sulfilimino group is a center of chirality. Stereoisomers can be obtained by customary separation methods, for example by chromatographic separation procedures, from the mixtures obtained in the preparation. It is also possible to selectively prepare stereoisomers by employing stereoselective reactions using optically active starting materials and/or auxiliaries. The invention also relates to all stereoisomers embraced by the formula (I) but not shown in their specific stereoform, and mixtures thereof.

The compounds of the formula (I) are capable of forming salts. Salt formation may occur by action of a base on those compounds of the formula (I) which carry an acidic hydrogen atom, for example in the case where R^(a) is a hydroxyl group or R^(h) is hydrogen. Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and also ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium hydroxide and potassium hydroxide, sodium carbonate and potassium carbonate and sodium bicarbonate and potassium bicarbonate. These salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, especially sodium salts and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NRR*R**R***]⁺ in which R, R*, R** and R*** independently of one another each denote an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl. Also suitable are alkylsulfonium and alkylsulfoxonium salts such as (C₁-C₄)-trialkylsulfonium and (C₁-C₄)-trialkylsulfoxonium salts.

By forming an adduct with a suitable inorganic or organic acid, for example mineral acids such as HCl, HBr, H₂SO₄, H₃PO₄ or HNO₃ or organic acids, for example carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid, or sulfonic acids such as p-toluenesulfonic acid, at a basic group, such as, for example, amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, the compounds of the formula (I) are capable of forming salts. In this case, the salts contain the conjugated base of the acid as anion.

Preference is given to compounds of the formula (I) in which

Q is a radical Q1, Q2, Q3, Q4 or Q5,

R^(a) is hydroxyl, R^(b), R^(c), R^(f) and R^(g) independently of one another are each hydrogen or (C₁-C₄)-alkyl, R^(d), R^(e) independently of one another are each hydrogen or (C₁-C₄)-alkyl or together with the carbon atom to which they are attached form a carbonyl group, R^(h) is hydrogen, R^(i) is (C₁-C₄)-alkyl, R^(k) is hydrogen, (C₁-C₄)-alkyl, (C₃-C₇)-cycloalkyl, A and Y independently of one another are each oxygen or (C₁-C₄)-alkylene which is substituted by n radicals R⁹, X is nitro, halogen, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S, (R⁵O)₂(O)P, R¹(O)C—(C₁-C₆)-alkyl, R¹O(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C—(C₁-C₆)-alkyl, NC—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl, (R¹)₂N—(C₁-C₆)-alkyl, R¹(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N—(C₁-C₆)-alkyl, R²O(O)C(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)_(n)S—(C₁-C₆)-alkyl, R¹O(O)₂S—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S—(C₁-C₆)-alkyl, (R⁵O)₂(O)P—(C₁-C₆)-alkyl, phenyl, heteroaryl, heterocyclyl, phenyl-(C₁-C₆)-alkyl, heteroaryl-(C₁-C₆)-alkyl, heterocyclyl-(C₁-C₆)-alkyl, where the six last-mentioned radicals are each substituted by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, R¹O, (R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl and where heterocyclyl carries n oxo groups, Z is hydrogen, nitro, halogen, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R¹ (O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S, (R⁵O)₂(O)P, R¹(O)C—(C₁-C₆)-alkyl, R¹O(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C—(C₁-C₆)-alkyl, NC—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl, (R¹)₂N—(C₁-C₆)-alkyl, R¹(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N—(C₁-C₆)-alkyl, R²O(O)C(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)_(n)S—(C₁-C₆)-alkyl, R¹O(O)₂S—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S—(C₁-C₆)-alkyl, (R⁵O)₂(O)P—(C₁-C₆)-alkyl, phenyl, heteroaryl, heterocyclyl, phenyl-(C₁-C₆)-alkyl, heteroaryl-(C₁-C₆)-alkyl, heterocyclyl-(C₁-C₆)-alkyl, where the six last-mentioned radicals are each substituted by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, R¹O, (R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl and where heterocyclyl carries n oxo groups, W is hydrogen, halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-alkyl-(O)_(n)S—, R¹O(O)C, (R¹)₂N, R¹(O)C(R¹)N or R²(O)₂S(R¹)N, R is (C₁-C₆)-alkyl which is in each case substituted by s radicals from the group consisting of halogen, cyano, (C₃-C₆)-cycloalkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C, R²(O)₂S(R¹)N(O)C, R¹O, (R¹)₂N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S and (R¹)₂N(O)C(R¹)N(O)₂S or is (C₃-C₆)-cycloalkyl which is in each case substituted by s radicals from the group consisting of halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R¹O(O)C and (R¹)₂N(O)C, R′ is hydrogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R¹(O)C, R²O(O)C, (R¹)₂N(O)C, R²(O)₂S, R¹(O)C—(C₁-C₆)-alkyl, R¹O(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl, (R¹)₂N—(C₁-C₆)-alkyl, R²(O)_(n)S—(C₁-C₆)-alkyl, R¹ is hydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, cycloalkyl-(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl, heteroaryl-(C₁-C₆)-alkyl, heterocyclyl, heterocyclyl-(C₁-C₆)-alkyl, phenyl-O—(C₁-C₆)-alkyl, heteroaryl-O—(C₁-C₆)-alkyl, heterocyclyl-O—(C₁-C₆)-alkyl, where the nine last-mentioned radicals are in each case substituted by s radicals from the group consisting of nitro, halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, R³O(O)C, (R³)₂N(O)C, R³O, (R³)₂N, R⁴(O)_(n)S and R³O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups, R² is (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, cycloalkyl-(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl, heteroaryl-(C₁-C₆)-alkyl, heterocyclyl, heterocyclyl-(C₁-C₆)-alkyl, phenyl-O—(C₁-C₆)-alkyl, heteroaryl-O—(C₁-C₆)-alkyl, heterocyclyl-O—(C₁-C₆)-alkyl, where the nine last-mentioned radicals are in each case substituted by s radicals from the group consisting of nitro, halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, R³O(O)C, (R³)₂N(O)C, R³O, (R³)₂N, R⁴(O)_(n)S and R³O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups, R³ is hydrogen or (C₁-C₆)-alkyl, R⁴ is (C₁-C₆)-alkyl, R⁵ is hydrogen or (C₁-C₄)-alkyl, R⁹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy or (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, n is 0, 1 or 2, s is 0, 1, 2 or 3, t is 0 or 1.

Particular preference is given to compounds of the formula (I) in which

Q is a radical Q1, Q2, Q3, Q4 or Q5,

R^(a) is hydroxyl, R^(b), R^(c), R^(f) and R^(g) independently of one another are each hydrogen or methyl, R^(d), R^(e) are hydrogen or together with the carbon atom to which they are attached form a carbonyl group, R^(h) is hydrogen, R^(i) is methyl or ethyl, R^(k) is hydrogen, methyl or cyclopropyl, A and Y independently of one another are each CH₂ or CH₂CH₂, X is nitro, halogen, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, heptafluoroisopropyl, cyclopropyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxymethyl, ethoxymethyl, methoxyethyl, methoxyethoxymethyl, methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl, Z is hydrogen, nitro, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, heptafluoroisopropyl, cyclopropyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl or methylsulfonyl, W is hydrogen, chlorine or methyl, R is methyl, ethyl or n-propyl, R′ is hydrogen or cyano, t is 0 or 1.

The compounds of the formula (I) according to the invention can be prepared from the corresponding thioethers of the formula (I-thioether) (Scheme 1). To this end, the thioether is converted, for example with cyanamide and an oxidizing agent (iodosobenzene diacetate, sodium hypochlorite or N-bromosuccinimide) into the corresponding sulfilimine, which can be oxidized further to the sulfoximine. Suitable for the oxidation to the sulfoximine are oxidizing agents such as, for example, meta-chlorperbenzoic acid, sodium permanganate or a mixture of sodium periodate and ruthenium trichloride. NH-Sulfoximines can be obtained, for example, from sulfoxides using sodium azide and sulfuric acid and can be functionalized at the nitrogen atom with reagents such as, for example cyanogen bromide, acid chlorides or acid anhydrides, chloroformic esters, nitric acid or other compounds. The oxidation of N-sulfonated sulfilimines to the corresponding sulfoximines can be achieved with hydrogen, for example. Alternatively, sulfoxides can be converted into N-acylated or N-sulfonated sulfoximines. The carboxamide or sulfonamide, respectively, can then be cleaved to give the NH-sulfoximine. Such synthesis methods for generating sulfilimines and sulfoximines from thioethers or for generating sulfoximines from sulfoxides or for derivatizing sulfilimines and sulfoximines, also of NH-sulfoximines, inter alia, are described, for example, in Bolm, C. Org. Lett. 2004, 6, 1305; Bolm, C. Org. Lett. 2007, 9, 3809; Bolm, C. Synthesis 2010, 17, 2922; Bolm, C. Adv. Synth. Catal. 2010, 352, 309, WO 2007/095229 A1, WO 2008/141843 A1, WO 2008/097235 A1, US 2008/0207910 A1, US 2008/0194634 A1 and US 2010/0056534 A1.

If required, protective groups have to be employed for such synthetic sequences to achieve sufficient selectivity. In particular the functionalization at the NH-sulfoximine competes in principle with the analogous functionalization at the amide nitrogen atom. The optimum procedure depends on the substitution pattern in question.

Compounds of the formula (I-thioether) and the formula (I-sulfoxide) are known and described, for example, in WO 2003/014071 A1, WO 2008/125214 A1, WO 2009/149806 A1, WO 2011012247 A1, WO 2011012247 A1, EP 0 609 798 A1 and EP 0 625 508 A1.

It may be expedient to change the order of reaction steps. Under certain conditions, sulfoximines and in particular sulfilimines are insufficiently stable (Bolm, C. Adv. Synth. Catal. 2010, 352, 309), so it may be advantageous, as shown in Scheme 1, to synthesize initially, at the thioether stage, the benzoyl derivative and to generate the sulfilimine or the sulfoximine from the thioether only at the end of the synthesis sequence. However, in the case of sufficient stability, it may, depending on the substitution pattern, also be expedient to generate first, at the benzoic acid stage (or at an even earlier stage) the sulfilimine of the sulfoximine from the thioether, and only then to convert the benzoic acid into its benzoyl derivative (Scheme 2). The conversion of benzoic acids into their benzoyl derivatives is known for numerous classes of structures not comprising a sulfilimino group or sulfoximino group and described, for example, in WO 2003/014071 A1, WO 2008/125214 A1, WO 2009/149806 A1, WO 2011012247 A1, WO 2011012247 A1, EP 0 609 798 A1 and EP 0 625 508 A1. Depending on the substitution pattern, this route to the compounds of the formula (I) according to the invention may be expedient.

In certain cases, it may be advantageous to use not the free benzoic acid but derivatives thereof for the reactions. Sometimes it is sufficient for the stability of a functional group to work only in acidic or only in basic media, that is to work only with the free benzoic acid or only with its salt. In many cases, esters such as methyl or ethyl esters are suitable. Frequently, tert-butyl esters effectively shield the carboxyl group sterically against nucleophilic reagents, and they are easily cleaved in acidic medium (T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd Edition, John Wiley & Sons, Inc. 1991, p. 227 ff.). Also suitable are radicals which are considerably more stable than carboxyl groups, which can, however, also be easily re-converted into the free carboxylic acids. These include, for example, oxazolines (T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd Edition, John Wiley & Sons, Inc. 1991, p. 265 ff.; Z. Hell et al, Tetrahedron Letters 43 (2002), 3985-3987).

The benzoic acids of the formulae (IIa) and (IIb) mentioned above and their ethyl esters, methyl esters and benzoyl chlorides are novel and are represented by the formula (II).

In formula (II), Q* is hydroxyl, ethoxy, methoxy or chlorine. R, R′, X, W, Z and t have the meanings given for formula (I). The compounds of the formula (II) are suitable in particular for preparing the compounds of the formula (I) according to the invention. The compounds of the formula (II) also form part of the subject matter of the present invention.

Work-up of the respective reaction mixtures is generally carried out by known methods, for example by crystallization, aqueous-extractive work-up, by chromatographic methods or by a combination of these methods.

Collections of compounds of the formula (I) and/or their salts which can be synthesized in accordance with the abovementioned reactions can also be prepared in a parallelized manner, which can be effected manually or in a partly or fully automated manner. Here, it is possible for example to automate the procedure of the reaction, the work-up or the purification of the products or intermediates. In total, this is understood as meaning a procedure as described for example by D. Tiebes in Combinatorial Chemistry—Synthesis, Analysis, Screening (Editor Günther Jung), Wiley 1999, on pages 1 to 34.

A number of commercially available apparatuses can be used for the parallelized reaction procedure and work-up, for example Calpyso reaction blocks from Barnstead International, Dubuque, Iowa 52004-0797, USA, or reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB 11 3AZ, England or MultiPROBE Automated Workstations from Perkin Elmar, Waltham, Mass. 02451, USA. Chromatographic apparatuses, for example from ISCO, Inc., 4700 Superior Street, Lincoln, Nebr. 68504, USA, are available, inter alia, for the parallelized purification of compounds of the formula (I) and their salts or of intermediates generated in the course of the preparation.

The apparatuses listed lead to a modular procedure in which the individual passes are automated, but manual operations must be carried out between the passes. This can be circumvented by the use of partly or fully integrated automation systems, where the relevant automation modules are operated by, for example, robots. Such automation systems can be obtained for example from Caliper, Hopkinton, Mass. 01748, USA.

The performance of individual, or a plurality of, synthesis steps can be aided by the use of polymer-supported reagents/scavenger resins. The specialist literature describes a series of experimental protocols, for example in ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).

Besides the methods described herein, the preparation of compounds of the formula (I) and their salts can be effected fully or in part by solid-phase-supported methods. For this purpose, individual intermediates, or all intermediates, of the synthesis or of a synthesis adapted to the relevant procedure are bound to a synthesis resin. Solid-phase-supported synthesis methods are described sufficiently in the specialist literature, for example Barry A. Bunin in “The Combinatorial Index”, Academic Press, 1998 and Combinatorial Chemistry—Synthesis, Analysis, Screening (Editor Guinther Jung), Wiley, 1999. The use of solid-phase-supported synthesis methods permits a series of protocols known from the literature, which, again, can be carried out manually or in an automated manner. For example, the reactions can be carried out by means of IRORI technology in microreactors from Nexus Biosystems, 12140 Community Road, Poway, Calif. 92064, USA.

Carrying out individual or a plurality of synthesis steps, both on a solid and in the liquid phase, can be aided by the use of microwave technology. A series of experimental protocols are described in the specialist literature, for example in Microwaves in Organic and Medicinal Chemistry (Editors C. O. Kappe and A. Stadler), Wiley, 2005. The preparation in accordance with the processes described herein generates compounds of the formula (I) and their salts in the form of substance collections, which are referred to as libraries. The present invention also relates to libraries which comprise at least two compounds of the formula (I) and their salts.

The compounds of the formula (I) according to the invention (and/or their salts), hereinbelow together referred to as “compounds according to the invention”, have an outstanding herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous annual harmful plants. The active substances also act efficiently on perennial harmful plants which produce shoots from rhizomes, rootstocks or other perennial organs and which are difficult to control.

The present invention therefore also relates to a method of controlling unwanted plants or for regulating the growth of plants, preferably in crops of plants, where one or more compound(s) according to the invention is/are applied to the plants (for example harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants), to the seeds (for example grains, seeds or vegetative propagules such as tubers or shoot parts with buds) or to the area on which the plants grow (for example the area under cultivation). In this context, the compounds according to the invention can be applied for example pre-planting (if appropriate also by incorporation into the soil), pre-emergence or post-emergence. Examples of individual representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the compounds according to the invention shall be mentioned, without the mention being intended as a limitation to certain species.

Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

If the compounds according to the invention are applied to the soil surface before germination, either the emergence of the weed seedlings is prevented completely or the weeds grow until they have reached the cotyledon stage, but then stop their growth and, finally, die completely after three to four weeks have elapsed.

When the active substances are applied post-emergence to the green plant parts, growth stops after the treatment, and the harmful plants remain in the growth stage of the time of application or die fully after a certain period of time, so that competition by weeds, which is harmful to the crop plants, is thus eliminated at an early point in time and in a sustained manner.

Although the compounds according to the invention display an outstanding herbicidal activity against monocotyledonous and dicotyledonous weeds, crop plants of economically important crops, for example dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, in particular Zea and Triticum, are damaged only to an insignificant extent, or not at all, depending on the structure of the respective compound according to the invention and its application rate. This is why the present compounds are highly suitable for the selective control of undesired plant growth in plant crops such as agriculturally useful plants or ornamentals.

Moreover, the compounds according to the invention (depending on their respective structure and the application rate applied) have outstanding growth-regulatory properties in crop plants. They engage in the plant metabolism in a regulatory fashion and can therefore be employed for the influencing, in a targeted manner, of plant constituents and for facilitating harvesting, such as, for example, by triggering desiccation and stunted growth. Moreover, they are also suitable for generally controlling and inhibiting undesired vegetative growth without destroying the plants in the process. Inhibiting the vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops since for example lodging can be reduced, or prevented completely, hereby.

Owing to their herbicidal and plant-growth-regulatory properties, the active substances can also be employed for controlling harmful plants in crops of genetically modified plants or plants which have been modified by conventional mutagenesis. As a rule, the transgenic plants are distinguished by especially advantageous properties, for example by resistances to certain pesticides, mainly certain herbicides, resistances to plant diseases or causative organisms of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties relate for example to the harvested material with regard to quantity, quality, storability, composition and specific constituents. Thus, transgenic plants with an increased starch content or a modified starch quality or those with a different fatty acid composition of the harvested material are known.

It is preferred to use the compounds according to the invention or their salts in economically important transgenic crops of useful plants and ornamentals, for example of cereals such as wheat, barley, rye, oats, sorghum and millet, rice, cassava and maize or else crops of sugar beet, cotton, soybean, oil seed rape, potato, tomato, peas and other vegetables. It is preferred to employ the compounds according to the invention as herbicides in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

Conventional ways of generating novel plants which, in comparison with existing plants, have modified properties are, for example, traditional breeding methods and the generation of mutants. Alternatively, novel plants with modified properties can be generated with the aid of recombinant methods (see, for example, EP-A-0221044, EP-A-0131624). For example, the following have been described in several cases:

-   -   recombinant modifications of crop plants for the purposes of         modifying the starch synthesized in the plants (for example WO         92/11376, WO 92/14827, WO 91/19806),     -   transgenic crop plants which are resistant to certain herbicides         of the glufosinate type (cf., for example, EP-A-0242236,         EP-A-242246) or of the glyphosate type (WO 92/00377) or of the         sulfonylurea type (EP-A-0257993, U.S. Pat. No. 5,013,659),     -   transgenic crop plants, for example cotton, which is capable of         producing Bacillus thuringiensis toxins (Bt toxins), which make         the plants resistant to certain pests (EP-A-0142924,         EP-A-0193259),     -   transgenic crop plants with a modified fatty acid composition         (WO 91/13972),     -   genetically modified crop plants with novel constituents or         secondary metabolites, for example novel phytoalexins, which         bring about an increased disease resistance (EPA 309862,         EPA0464461),     -   genetically modified plants with reduced photorespiration which         feature higher yields and higher stress tolerance (EPA 0305398),     -   transgenic crop plants which produce pharmaceutically or         diagnostically important proteins (“molecular pharming”),     -   transgenic crop plants which are distinguished by higher yields         or better quality,     -   transgenic crop plants which are distinguished by a combination,         for example of the abovementioned novel properties (“gene         stacking”).

A large number of molecular-biological techniques by means of which novel transgenic plants with modified properties can be generated are known in principle; see, for example, I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg. or Christou, “Trends in Plant Science” 1 (1996) 423-431).

To carry out such recombinant manipulations, it is possible to introduce nucleic acid molecules into plasmids, which permit a mutagenesis or sequence modification by recombination of DNA sequences. For example, base substitutions can be carried out, part-sequences can be removed, or natural or synthetic sequences may be added with the aid of standard methods. To link the DNA fragments with one another, it is possible to add adapters or linkers to the fragments; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Gene und Klone”, V C H Weinheim 2nd ed., 1996

The generation of plant cells with a reduced activity for a gene product can be achieved for example by the expression of at least one corresponding antisense RNA, a sense RNA for achieving a cosuppression effect or by the expression of at least one correspondingly constructed ribozyme, which specifically cleaves transcripts of the abovementioned gene product. To do this, it is possible firstly to use DNA molecules which comprise all of the coding sequence of a gene product, including any flanking sequences which may be present, or else DNA molecules which only comprise parts of the coding sequence, it being necessary for these parts to be long enough to bring about an antisense effect in the cells. It is also possible to use DNA sequences which have a high degree of homology with the coding sequences of a gene product, but which are not entirely identical.

When expressing nucleic acid molecules in plants, the protein synthesized may be localized in any compartment of the plant cell. In order to achieve localization in a particular compartment, however, it is possible for example to link the coding region to DNA sequences which ensure the localization in a specific compartment. Such sequences are known to the skilled worker (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). The nucleic acid molecules can also be expressed in the organelles of the plant cells.

The transgenic plant cells can be regenerated by known techniques to give intact plants. In principle, the transgenic plants may be plants of any plant species, that is to say both monocotyledonous and dicotyledonous plants.

Thus, transgenic plants can be obtained which feature modified properties as the result of overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or expression of heterologous (=foreign) genes or gene sequences.

It is preferred to employ the compounds according to the invention in transgenic crops which are resistant to growth regulators such as, for example, dicamba, or against herbicides which inhibit essential plant enzymes, for example acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD), or against herbicides from the group of the sulfonylureas, glyphosate, glufosinate or benzoylisoxazoles and analogous active substances. When the active substances according to the invention are used in transgenic crops, effects are frequently observed—in addition to the effects on harmful plants which can be observed in other crops—which are specific for the application in the transgenic crop in question, for example a modified or specifically widened spectrum of weeds which can be controlled, modified application rates which may be employed for application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and an effect on growth and yield of the transgenic crop plants.

The invention therefore also relates to the use of the compounds according to the invention as herbicides for controlling harmful plants in transgenic crop plants.

The compounds according to the invention can be employed in the customary preparations in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules. The invention therefore also relates to herbicidal and plant-growth-regulating compositions which comprise the compounds according to the invention.

The compounds according to the invention can be formulated in various ways, depending on the prevailing biological and/or physico-chemical parameters. Examples of possible formulations are: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), seed-dressing products, granules for application by broadcasting and on the soil, granules (GR) in the form of microgranules, spray granules, coated granules and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

These individual types of formulation are known in principle and are described, for example, in: Winnacker-Kuichler, “Chemische Technologie” [Chemical technology], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986; Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y., 1973; K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

The formulation auxiliaries required, such as inert materials, surfactants, solvents and further additives, are also known and are described, for example, in: Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J., H. v. Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, “Grenzflächenaktive Äthylenoxidaddukte” [Interface-active ethylene oxide adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler, “Chemische Technologie” [Chemical technology], volume 7, C. Hanser Verlag Munich, 4th Ed. 1986.

Based on these formulations, it is also possible to prepare combinations with other pesticidally active substances such as, for example, insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and/or growth regulators, for example in the form of a ready mix or a tank mix. Suitable safeners are, for example, mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl and dichlormid.

Wettable powders are preparations which are uniformly dispersible in water and which, besides the active substance, also comprise ionic and/or nonionic surfactants (wetters, dispersants), for example polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2′-dinaphthylmethane-6,6′-disulfonate, sodium dibutylnaphthalenesulfonate or else sodium oleoylmethyltaurinate, besides a diluent or inert substance. To prepare the wettable powders, the herbicidally active substances are ground finely, for example in customary apparatuses such as hammer mills, blower mills and air-jet mills, and mixed with the formulation auxiliaries, either simultaneously or subsequently.

Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with addition of one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are: calcium alkylarylsulfonates such as calcium dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylarylpolyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensates, alkyl polyethers, sorbitan esters such as, for example, sorbitan fatty acid esters or polyoxyethylene sorbitan esters such as, for example, polyoxyethylene sorbitan fatty acid esters.

Dusts are obtained by grinding the active substance with finely divided solid materials such as, for example, talcum, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates can be water- or oil-based. They can be prepared for example by wet-grinding by means of commercially available bead mills, if appropriate with addition of surfactants as already listed above for example in the case of the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be prepared for example by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and, if appropriate, surfactants, as have already been mentioned for example above for the other formulation types.

Granules can be prepared either by spraying the active substance onto adsorptive, granulated inert material, or by applying active substance concentrates to the surface of carriers such as sand, kaolinites or granulated inert material with the aid of stickers, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils. Suitable active substances can also be granulated in the manner which is customary for the production of fertilizer granules, if desired as a mixture with fertilizers.

Water-dispersible granules are generally prepared by customary methods such as spray drying, fluidized-bed granulation, disk granulation, mixing with high-speed stirrers, and extrusion without solid inert material.

To prepare disk granules, fluidized-bed granules, extruder granules and spray granules, see, for example, methods in “Spray-Drying Handbook” 3rd ed. 1979, G. Goodwin Ltd., London; J. E. Browning, “Agglomeration”, Chemical and Engineering 1967, pages 147 et seq.; “Perry's Chemical Engineer's Handbook”, 5th Ed., McGraw-Hill, New York 1973, p. 8-57.

For further details of the formulation of crop protection products see, for example, G. C. Klingman, “Weed Control as a Science”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J. D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

As a rule, the agrochemical preparations comprise from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention. In wettable powders, the active substance concentration is, for example, approximately 10 to 90% by weight, the remainder to 100% by weight being composed of customary formulation constituents. In the case of emulsifiable concentrates, the active substance concentration can amount to approximately 1 to 90, preferably 5 to 80% by weight. Formulations in the form of dusts comprise from 1 to 30% by weight of active substance, preferably in most cases from 5 to 20% by weight of active substance, and sprayable solutions comprise approximately from 0.05 to 80, preferably from 2 to 50% by weight of active substance. In the case of water-dispersible granules, the active substance content depends partly on whether the active compound is in liquid or solid form, and on the granulation auxiliaries, fillers and the like which are being used. In the case of the water-dispersible granules, for example, the active substance content is between 1 and 95% by weight, preferably between 10 and 80% by weight.

In addition, the active substance formulations mentioned comprise, if appropriate, the auxiliaries which are conventional in each case, such as stickers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, antifoams, evaporation inhibitors, and pH and viscosity regulators.

Based on these formulations, it is also possible to prepare combinations with other pesticidally active substances such as, for example, insecticides, acaricides, herbicides, fungicides, and with safeners, fertilizers and/or growth regulators, for example in the form of a ready mix or a tank mix.

Active substances which can be employed in combination with the compounds according to the invention in mixed formulations or in the tank mix are, for example, known active substances which are based on the inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoen desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as are described in, for example, Weed Research 26 (1986) 441-445 or “The Pesticide Manual”, 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2003 and the literature cited therein. Known herbicides or plant growth regulators which can be combined with the compounds according to the invention are, for example, the following active substances (the compounds are either designated by the common name according to the International Organization for Standardization (ISO) or by a chemical name, if appropriate together with the code number) and always comprise all use forms such as acids, salts, esters and isomers such as stereoisomers and optical isomers.

For use, the formulations, which are present in commercially available form, if appropriate, are diluted in the customary manner, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Preparations in the form of dusts, soil granules, granules for broadcasting, and sprayable solutions, are usually not diluted further with further inert substances prior to use.

The application rate required of the compounds of the formula (I) varies as a function of the external conditions such as temperature, humidity, the nature of the herbicide used and the like. It can vary within wide limits, for example between 0.001 and 1.0 kg/ha and more of active substance, but it is preferably between 0.005 and 750 g/ha.

The examples which follow illustrate the invention.

A. CHEMICAL EXAMPLES Synthesis of 5-hydroxy-1,3-dimethyl-4-[3-(N-cyano-S-methylsulfonimidoyl)-2-methoxy-4-(trifluoromethyl)benzoyl]pyrazole (Table Example No. 4-160) Step 1: Synthesis of 3-(N-cyano-S-methylsulfonimidoyl)-2-methoxy-4-(trifluoromethyl)benzoic acid (Table Example No. 15-28)

3.71 g (33.1 mmol) of potassium tert-butoxide were added to a solution of 4.00 g (15.0 mmol) of 2-methoxy-3-(methylsulfanyl)-4-(trifluoromethyl)benzoic acid in 250 ml of methanol. The mixture was stirred for 10 minutes, and 1.07 g (25.5 mmol) of cyanamide and 4.81 g (27.0 mmol) of N-bromsuccinimide were then added in succession. The contents was then stirred at RT for 2 h. The mixture was then freed from the solvent on a rotary evaporator and the residue was taken up in a mixture of in each case 120 ml of acetonitrile and water. 7.21 g (45.1 mmol) of sodium permanganate monohydrate were added, and the mixture was stirred at RT for one week. During this week, both after one day and after a further day, in each case 3.6 g (22.5 mmol) of sodium permanganate monohydrate were added. For work-up, a 10% by weight strength solution of sodium bisulfate was added. On a rotary evaporator, at a temperature of at most 30° C., the solvent was substantially removed. The residue was cooled in an ice bath and then acidified with 1 M hydrochloric acid. The mixture was extracted three times with ice-cold dichloromethane. The combined organic phases were freed from the solvent on a rotary evaporator and the residue was purified chromatographically, which gave 1.30 g of product of a purity of 80% by weight.

Step 2: Synthesis of 5-hydroxy-1,3-dimethyl-4-[3-(N-cyano-S-methylsulfonimidoyl)-2-methoxy-4-(trifluoromethyl)benzoyl]pyrazole

165 mg (75% by weight; 0.384 mmol) of 3-(N-cyano-S-methylsulfonimidoyl)-2-methoxy-4-(trifluormethyl)benzoic acid and 68.9 mg (0.614 mmol) of 5-hydroxy-1,3-dimethylpyrazole were initially charged in 20 ml of dichlormethane, and 128 mg (0.666 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added. The mixture was stirred at RT for 16 h and, for work-up, washed with 1 M hydrochloric acid. After phase separation, the organic phase was dried, filtered and freed from the solvent on a rotary evaporator. The residue was purified chromatographically and the intermediate obtained was then dissolved in 15 ml of acetonitrile. 104 mg (1.02 mmol) of triethylamine, eight drops of trimethylcyanide and a spatula tip of potassium cyanide were then added. The mixture was stirred at RT for 16 h and, for work-up, freed from the solvent. The residue was taken up in dichloromethane and washed with 3 ml of 1M hydrochloric acid. After phase separation, the organic phase was freed from the solvent and the residue was purified chromatographically, which gave 31.3 mg of 5-hydroxy-1,3-dimethyl-4-[3-(N-cyano-S-methylsulfonimidoyl)-2-methoxy-4-(trifluoromethyl)benzoyl]pyrazole in a purity of 85% by weight.

The examples listed in the tables hereinbelow were prepared analogously to abovementioned methods or are obtainable analogously to abovementioned methods.

These compounds are very particularly preferred.

The abbreviations used are:

Et=ethyl Me=methyl n-Pr=n-propyl i-Pr=isopropyl c-Pr=cyclopropyl Ph=phenyl

TABLE 1 Compounds according to the invention of the formula (I) in which Q is Q1, R^(a) is a hydroxyl group, the radicals R^(b), R^(c), R^(d), R^(e), R^(f), R^(g) and W are each hydrogen, t = 1 and the other radicals have the meanings indicated in the table

No. X Z R R′ Physical data (¹H NMR) 1-1  Me Me Me H 1-2  Me F Me H 1-3  Me Cl Me H 1-4  Me Br Me H 1-5  Me I Me H 1-6  Me CF₃ Me H 1-7  Me CHF₂ Me H 1-8  Me CF₂Cl Me H 1-9  Me OMe Me H 1-10  Me NO₂ Me H 1-11  Me SO₂Me Me H 1-12  Cl Me Me H 1-13  Cl F Me H 1-14  Cl Cl Me H 1-15  Cl Br Me H 1-16  Cl I Me H 1-17  Cl CF₃ Me H 1-18  Cl CHF₂ Me H 1-19  Cl CF₂Cl Me H 1-20  Cl OMe Me H 1-21  Cl NO₂ Me H 1-22  Cl SO₂Me Me H 1-23  OMe Me Me H 1-24  OMe F Me H 1-25  OMe Cl Me H 1-26  OMe Br Me H 1-27  OMe I Me H 1-28  OMe CF₃ Me H 1-29  OMe CHF₂ Me H 1-30  OMe CF₂Cl Me H 1-31  OMe OMe Me H 1-32  OMe NO₂ Me H 1-33  OMe SO₂Me Me H 1-34  SO₂Me Me Me H 1-35  SO₂Me F Me H 1-36  SO₂Me Cl Me H 1-37  SO₂Me Br Me H 1-38  SO₂Me I Me H 1-39  SO₂Me CF₃ Me H 1-40  SO₂Me CHF₂ Me H 1-41  SO₂Me CF₂Cl Me H 1-42  SO₂Me OMe Me H 1-43  SO₂Me NO₂ Me H 1-44  SO₂Me SO₂Me Me H 1-45  Me Me Et H 1-46  Me F Et H 1-47  Me Cl Et H 1-48  Me Br Et H 1-49  Me I Et H 1-50  Me CF₃ Et H 1-51  Me CHF₂ Et H 1-52  Me CF₂Cl Et H 1-53  Me OMe Et H 1-54  Me NO₂ Et H 1-55  Me SO₂Me Et H 1-56  Cl Me Et H 1-57  Cl F Et H 1-58  Cl Cl Et H 1-59  Cl Br Et H 1-60  Cl I Et H 1-61  Cl CF₃ Et H 1-62  Cl CHF₂ Et H 1-63  Cl CF₂Cl Et H 1-64  Cl OMe Et H 1-65  Cl NO₂ Et H 1-66  Cl SO₂Me Et H 1-67  OMe Me Et H 1-68  OMe F Et H 1-69  OMe Cl Et H 1-70  OMe Br Et H 1-71  OMe I Et H 1-72  OMe CF₃ Et H 1-73  OMe CHF₂ Et H 1-74  OMe CF₂Cl Et H 1-75  OMe OMe Et H 1-76  OMe NO₂ Et H 1-77  OMe SO₂Me Et H 1-78  SO₂Me Me Et H 1-79  SO₂Me F Et H 1-80  SO₂Me Cl Et H 1-81  SO₂Me Br Et H 1-82  SO₂Me I Et H 1-83  SO₂Me CF₃ Et H 1-84  SO₂Me CHF₂ Et H 1-85  SO₂Me CF₂Cl Et H 1-86  SO₂Me OMe Et H 1-87  SO₂Me NO₂ Et H 1-88  SO₂Me SO₂Me Et H 1-89  Me Me CH₂CH₂OMe H 1-90  Me F CH₂CH₂OMe H 1-91  Me Cl CH₂CH₂OMe H 1-92  Me Br CH₂CH₂OMe H 1-93  Me I CH₂CH₂OMe H 1-94  Me CF₃ CH₂CH₂OMe H 1-95  Me CHF₂ CH₂CH₂OMe H 1-96  Me CF₂Cl CH₂CH₂OMe H 1-97  Me OMe CH₂CH₂OMe H 1-98  Me NO₂ CH₂CH₂OMe H 1-99  Me SO₂Me CH₂CH₂OMe H 1-100 Cl Me CH₂CH₂OMe H 1-101 Cl F CH₂CH₂OMe H 1-102 Cl Cl CH₂CH₂OMe H 1-103 Cl Br CH₂CH₂OMe H 1-104 Cl I CH₂CH₂OMe H 1-105 Cl CF₃ CH₂CH₂OMe H 1-106 Cl CHF₂ CH₂CH₂OMe H 1-107 Cl CF₂Cl CH₂CH₂OMe H 1-108 Cl OMe CH₂CH₂OMe H 1-109 Cl NO₂ CH₂CH₂OMe H 1-110 Cl SO₂Me CH₂CH₂OMe H 1-111 OMe Me CH₂CH₂OMe H 1-112 OMe F CH₂CH₂OMe H 1-113 OMe Cl CH₂CH₂OMe H 1-114 OMe Br CH₂CH₂OMe H 1-115 OMe I CH₂CH₂OMe H 1-116 OMe CF₃ CH₂CH₂OMe H 1-117 OMe CHF₂ CH₂CH₂OMe H 1-118 OMe CF₂Cl CH₂CH₂OMe H 1-119 OMe OMe CH₂CH₂OMe H 1-120 OMe NO₂ CH₂CH₂OMe H 1-121 OMe SO₂Me CH₂CH₂OMe H 1-122 SO₂Me Me CH₂CH₂OMe H 1-123 SO₂Me F CH₂CH₂OMe H 1-124 SO₂Me Cl CH₂CH₂OMe H 1-125 SO₂Me Br CH₂CH₂OMe H 1-126 SO₂Me I CH₂CH₂OMe H 1-127 SO₂Me CF₃ CH₂CH₂OMe H 1-128 SO₂Me CHF₂ CH₂CH₂OMe H 1-129 SO₂Me CF₂Cl CH₂CH₂OMe H 1-130 SO₂Me OMe CH₂CH₂OMe H 1-131 SO₂Me NO₂ CH₂CH₂OMe H 1-132 SO₂Me SO₂Me CH₂CH₂OMe H 1-133 Me Me Me CN 1-134 Me F Me CN 1-135 Me Cl Me CN 1-136 Me Br Me CN 1-137 Me I Me CN 1-138 Me CF₃ Me CN 1-139 Me CHF₂ Me CN 1-140 Me CF₂Cl Me CN 1-141 Me OMe Me CN 1-142 Me NO₂ Me CN 1-143 Me SO₂Me Me CN 1-144 Cl Me Me CN 1-145 Cl F Me CN 1-146 Cl Cl Me CN 1-147 Cl Br Me CN 1-148 Cl I Me CN 1-149 Cl CF₃ Me CN 1-150 Cl CHF₂ Me CN 1-151 Cl CF₂Cl Me CN 1-152 Cl OMe Me CN 1-153 Cl NO₂ Me CN 1-154 Cl SO₂Me Me CN 1-155 OMe Me Me CN 1-156 OMe F Me CN 1-157 OMe Cl Me CN 1-158 OMe Br Me CN 1-159 OMe I Me CN 1-160 OMe CF₃ Me CN 1-161 OMe CHF₂ Me CN 1-162 OMe CF₂Cl Me CN 1-163 OMe OMe Me CN 1-164 OMe NO₂ Me CN 1-165 OMe SO₂Me Me CN 1-166 SO₂Me Me Me CN 1-167 SO₂Me F Me CN 1-168 SO₂Me Cl Me CN 1-169 SO₂Me Br Me CN 1-170 SO₂Me I Me CN 1-171 SO₂Me CF₃ Me CN 1-172 SO₂Me CHF₂ Me CN 1-173 SO₂Me CF₂Cl Me CN 1-174 SO₂Me OMe Me CN 1-175 SO₂Me NO₂ Me CN 1-176 SO₂Me SO₂Me Me CN 1-177 Me Me Et CN 1-178 Me F Et CN 1-179 Me Cl Et CN 1-180 Me Br Et CN 1-181 Me I Et CN 1-182 Me CF₃ Et CN 1-183 Me CHF₂ Et CN 1-184 Me CF₂Cl Et CN 1-185 Me OMe Et CN 1-186 Me NO₂ Et CN 1-187 Me SO₂Me Et CN 1-188 Cl Me Et CN 1-189 Cl F Et CN 1-190 Cl Cl Et CN 1-191 Cl Br Et CN 1-192 Cl I Et CN 1-193 Cl CF₃ Et CN 1-194 Cl CHF₂ Et CN 1-195 Cl CF₂Cl Et CN 1-196 Cl OMe Et CN 1-197 Cl NO₂ Et CN 1-198 Cl SO₂Me Et CN 1-199 OMe Me Et CN 1-200 OMe F Et CN 1-201 OMe Cl Et CN 1-202 OMe Br Et CN 1-203 OMe I Et CN 1-204 OMe CF₃ Et CN 1-205 OMe CHF₂ Et CN 1-206 OMe CF₂Cl Et CN 1-207 OMe OMe Et CN 1-208 OMe NO₂ Et CN 1-209 OMe SO₂Me Et CN 1-210 SO₂Me Me Et CN 1-211 SO₂Me F Et CN 1-212 SO₂Me Cl Et CN 1-213 SO₂Me Br Et CN 1-214 SO₂Me I Et CN 1-215 SO₂Me CF₃ Et CN 1-216 SO₂Me CHF₂ Et CN 1-217 SO₂Me CF₂Cl Et CN 1-218 SO₂Me OMe Et CN 1-219 SO₂Me NO₂ Et CN 1-220 SO₂Me SO₂Me Et CN 1-221 Me Me CH₂CH₂OMe CN 1-222 Me F CH₂CH₂OMe CN 1-223 Me Cl CH₂CH₂OMe CN 1-224 Me Br CH₂CH₂OMe CN 1-225 Me I CH₂CH₂OMe CN 1-226 Me CF₃ CH₂CH₂OMe CN 1-227 Me CHF₂ CH₂CH₂OMe CN 1-228 Me CF₂Cl CH₂CH₂OMe CN 1-229 Me OMe CH₂CH₂OMe CN 1-230 Me NO₂ CH₂CH₂OMe CN 1-231 Me SO₂Me CH₂CH₂OMe CN 1-232 Cl Me CH₂CH₂OMe CN 1-233 Cl F CH₂CH₂OMe CN 1-234 Cl Cl CH₂CH₂OMe CN 1-235 Cl Br CH₂CH₂OMe CN 1-236 Cl I CH₂CH₂OMe CN 1-237 Cl CF₃ CH₂CH₂OMe CN 1-238 Cl CHF₂ CH₂CH₂OMe CN 1-239 Cl CF₂Cl CH₂CH₂OMe CN 1-240 Cl OMe CH₂CH₂OMe CN 1-241 Cl NO₂ CH₂CH₂OMe CN 1-242 Cl SO₂Me CH₂CH₂OMe CN 1-243 OMe Me CH₂CH₂OMe CN 1-244 OMe F CH₂CH₂OMe CN 1-245 OMe Cl CH₂CH₂OMe CN 1-246 OMe Br CH₂CH₂OMe CN 1-247 OMe I CH₂CH₂OMe CN 1-248 OMe CF₃ CH₂CH₂OMe CN 1-249 OMe CHF₂ CH₂CH₂OMe CN 1-250 OMe CF₂Cl CH₂CH₂OMe CN 1-251 OMe OMe CH₂CH₂OMe CN 1-252 OMe NO₂ CH₂CH₂OMe CN 1-253 OMe SO₂Me CH₂CH₂OMe CN 1-254 SO₂Me Me CH₂CH₂OMe CN 1-255 SO₂Me F CH₂CH₂OMe CN 1-256 SO₂Me Cl CH₂CH₂OMe CN 1-257 SO₂Me Br CH₂CH₂OMe CN 1-258 SO₂Me I CH₂CH₂OMe CN 1-259 SO₂Me CF₃ CH₂CH₂OMe CN 1-260 SO₂Me CHF₂ CH₂CH₂OMe CN 1-261 SO₂Me CF₂Cl CH₂CH₂OMe CN 1-262 SO₂Me OMe CH₂CH₂OMe CN 1-263 SO₂Me NO₂ CH₂CH₂OMe CN 1-264 SO₂Me SO₂Me CH₂CH₂OMe CN

TABLE 2 Compounds according to the invention of the formula (I) in which Q is Q2, R^(a) is a hydroxyl group, R^(b), R^(f) and W are each hydrogen, A is CH₂CH₂, Y is CH₂, t = 1 and the other radicals have the meanings indicated in the table

No. X Z R R′ Physical data (¹H NMR) 2-1  Me Me Me H 2-2  Me F Me H 2-3  Me Cl Me H 2-4  Me Br Me H 2-5  Me I Me H 2-6  Me CF₃ Me H 2-7  Me CHF₂ Me H 2-8  Me CF₂Cl Me H 2-9  Me OMe Me H 2-10  Me NO₂ Me H 2-11  Me SO₂Me Me H 2-12  Cl Me Me H 2-13  Cl F Me H 2-14  Cl Cl Me H 2-15  Cl Br Me H 2-16  Cl I Me H 2-17  Cl CF₃ Me H 2-18  Cl CHF₂ Me H 2-19  Cl CF₂Cl Me H 2-20  Cl OMe Me H 2-21  Cl NO₂ Me H 2-22  Cl SO₂Me Me H 2-23  OMe Me Me H 2-24  OMe F Me H 2-25  OMe Cl Me H 2-26  OMe Br Me H 2-27  OMe I Me H 2-28  OMe CF₃ Me H 2-29  OMe CHF₂ Me H 2-30  OMe CF₂Cl Me H 2-31  OMe OMe Me H 2-32  OMe NO₂ Me H 2-33  OMe SO₂Me Me H 2-34  SO₂Me Me Me H 2-35  SO₂Me F Me H 2-36  SO₂Me Cl Me H 2-37  SO₂Me Br Me H 2-38  SO₂Me I Me H 2-39  SO₂Me CF₃ Me H 2-40  SO₂Me CHF₂ Me H 2-41  SO₂Me CF₂Cl Me H 2-42  SO₂Me OMe Me H 2-43  SO₂Me NO₂ Me H 2-44  SO₂Me SO₂Me Me H 2-45  Me Me Et H 2-46  Me F Et H 2-47  Me Cl Et H 2-48  Me Br Et H 2-49  Me I Et H 2-50  Me CF₃ Et H 2-51  Me CHF₂ Et H 2-52  Me CF₂Cl Et H 2-53  Me OMe Et H 2-54  Me NO₂ Et H 2-55  Me SO₂Me Et H 2-56  Cl Me Et H 2-57  Cl F Et H 2-58  Cl Cl Et H 2-59  Cl Br Et H 2-60  Cl I Et H 2-61  Cl CF₃ Et H 2-62  Cl CHF₂ Et H 2-63  Cl CF₂Cl Et H 2-64  Cl OMe Et H 2-65  Cl NO₂ Et H 2-66  Cl SO₂Me Et H 2-67  OMe Me Et H 2-68  OMe F Et H 2-69  OMe Cl Et H 2-70  OMe Br Et H 2-71  OMe I Et H 2-72  OMe CF₃ Et H 2-73  OMe CHF₂ Et H 2-74  OMe CF₂Cl Et H 2-75  OMe OMe Et H 2-76  OMe NO₂ Et H 2-77  OMe SO₂Me Et H 2-78  SO₂Me Me Et H 2-79  SO₂Me F Et H 2-80  SO₂Me Cl Et H 2-81  SO₂Me Br Et H 2-82  SO₂Me I Et H 2-83  SO₂Me CF₃ Et H 2-84  SO₂Me CHF₂ Et H 2-85  SO₂Me CF₂Cl Et H 2-86  SO₂Me OMe Et H 2-87  SO₂Me NO₂ Et H 2-88  SO₂Me SO₂Me Et H 2-89  Me Me CH₂CH₂OMe H 2-90  Me F CH₂CH₂OMe H 2-91  Me Cl CH₂CH₂OMe H 2-92  Me Br CH₂CH₂OMe H 2-93  Me I CH₂CH₂OMe H 2-94  Me CF₃ CH₂CH₂OMe H 2-95  Me CHF₂ CH₂CH₂OMe H 2-96  Me CF₂Cl CH₂CH₂OMe H 2-97  Me OMe CH₂CH₂OMe H 2-98  Me NO₂ CH₂CH₂OMe H 2-99  Me SO₂Me CH₂CH₂OMe H 2-100 Cl Me CH₂CH₂OMe H 2-101 Cl F CH₂CH₂OMe H 2-102 Cl Cl CH₂CH₂OMe H 2-103 Cl Br CH₂CH₂OMe H 2-104 Cl I CH₂CH₂OMe H 2-105 Cl CF₃ CH₂CH₂OMe H 2-106 Cl CHF₂ CH₂CH₂OMe H 2-107 Cl CF₂Cl CH₂CH₂OMe H 2-108 Cl OMe CH₂CH₂OMe H 2-109 Cl NO₂ CH₂CH₂OMe H 2-110 Cl SO₂Me CH₂CH₂OMe H 2-111 OMe Me CH₂CH₂OMe H 2-112 OMe F CH₂CH₂OMe H 2-113 OMe Cl CH₂CH₂OMe H 2-114 OMe Br CH₂CH₂OMe H 2-115 OMe I CH₂CH₂OMe H 2-116 OMe CF₃ CH₂CH₂OMe H 2-117 OMe CHF₂ CH₂CH₂OMe H 2-118 OMe CF₂Cl CH₂CH₂OMe H 2-119 OMe OMe CH₂CH₂OMe H 2-120 OMe NO₂ CH₂CH₂OMe H 2-121 OMe SO₂Me CH₂CH₂OMe H 2-122 SO₂Me Me CH₂CH₂OMe H 2-123 SO₂Me F CH₂CH₂OMe H 2-124 SO₂Me Cl CH₂CH₂OMe H 2-125 SO₂Me Br CH₂CH₂OMe H 2-126 SO₂Me I CH₂CH₂OMe H 2-127 SO₂Me CF₃ CH₂CH₂OMe H 2-128 SO₂Me CHF₂ CH₂CH₂OMe H 2-129 SO₂Me CF₂Cl CH₂CH₂OMe H 2-130 SO₂Me OMe CH₂CH₂OMe H 2-131 SO₂Me NO₂ CH₂CH₂OMe H 2-132 SO₂Me SO₂Me CH₂CH₂OMe H 2-133 Me Me Me CN 2-134 Me F Me CN 2-135 Me Cl Me CN 2-136 Me Br Me CN 2-137 Me I Me CN 2-138 Me CF₃ Me CN 2-139 Me CHF₂ Me CN 2-140 Me CF₂Cl Me CN 2-141 Me OMe Me CN 2-142 Me NO₂ Me CN 2-143 Me SO₂Me Me CN 2-144 Cl Me Me CN 2-145 Cl F Me CN 2-146 Cl Cl Me CN 2-147 Cl Br Me CN 2-148 Cl I Me CN 2-149 Cl CF₃ Me CN 2-150 Cl CHF₂ Me CN 2-151 Cl CF₂Cl Me CN 2-152 Cl OMe Me CN 2-153 Cl NO₂ Me CN 2-154 Cl SO₂Me Me CN 2-155 OMe Me Me CN 2-156 OMe F Me CN 2-157 OMe Cl Me CN 2-158 OMe Br Me CN 2-159 OMe I Me CN 2-160 OMe CF₃ Me CN (400 MHz, CDCl₃ δ, ppm) 7.81 (m, 1H), 7.65 (d, 1H), 3.91 + 3.88 (s + s, 3H), 3.65 + 3.62 (s + s, 3H), 3.21 (m, 1H), 2.91 (m, 1H) 2-161 OMe CHF₂ Me CN 2-162 OMe CF₂Cl Me CN 2-163 OMe OMe Me CN 2-164 OMe NO₂ Me CN 2-165 OMe SO₂Me Me CN 2-166 SO₂Me Me Me CN 2-167 SO₂Me F Me CN 2-168 SO₂Me Cl Me CN 2-169 SO₂Me Br Me CN 2-170 SO₂Me I Me CN 2-171 SO₂Me CF₃ Me CN 2-172 SO₂Me CHF₂ Me CN 2-173 SO₂Me CF₂Cl Me CN 2-174 SO₂Me OMe Me CN 2-175 SO₂Me NO₂ Me CN 2-176 SO₂Me SO₂Me Me CN 2-177 Me Me Et CN 2-178 Me F Et CN 2-179 Me Cl Et CN 2-180 Me Br Et CN 2-181 Me I Et CN 2-182 Me CF₃ Et CN 2-183 Me CHF₂ Et CN 2-184 Me CF₂Cl Et CN 2-185 Me OMe Et CN 2-186 Me NO₂ Et CN 2-187 Me SO₂Me Et CN 2-188 Cl Me Et CN 2-189 Cl F Et CN 2-190 Cl Cl Et CN 2-191 Cl Br Et CN 2-192 Cl I Et CN 2-193 Cl CF₃ Et CN 2-194 Cl CHF₂ Et CN 2-195 Cl CF₂Cl Et CN 2-196 Cl OMe Et CN 2-197 Cl NO₂ Et CN 2-198 Cl SO₂Me Et CN 2-199 OMe Me Et CN 2-200 OMe F Et CN 2-201 OMe Cl Et CN 2-202 OMe Br Et CN 2-203 OMe I Et CN 2-204 OMe CF₃ Et CN 2-205 OMe CHF₂ Et CN 2-206 OMe CF₂Cl Et CN 2-207 OMe OMe Et CN 2-208 OMe NO₂ Et CN 2-209 OMe SO₂Me Et CN 2-210 SO₂Me Me Et CN 2-211 SO₂Me F Et CN 2-212 SO₂Me Cl Et CN 2-213 SO₂Me Br Et CN 2-214 SO₂Me I Et CN 2-215 SO₂Me CF₃ Et CN 2-216 SO₂Me CHF₂ Et CN 2-217 SO₂Me CF₂Cl Et CN 2-218 SO₂Me OMe Et CN 2-219 SO₂Me NO₂ Et CN 2-220 SO₂Me SO₂Me Et CN 2-221 Me Me CH₂CH₂OMe CN 2-222 Me F CH₂CH₂OMe CN 2-223 Me Cl CH₂CH₂OMe CN 2-224 Me Br CH₂CH₂OMe CN 2-225 Me I CH₂CH₂OMe CN 2-226 Me CF₃ CH₂CH₂OMe CN 2-227 Me CHF₂ CH₂CH₂OMe CN 2-228 Me CF₂Cl CH₂CH₂OMe CN 2-229 Me OMe CH₂CH₂OMe CN 2-230 Me NO₂ CH₂CH₂OMe CN 2-231 Me SO₂Me CH₂CH₂OMe CN 2-232 Cl Me CH₂CH₂OMe CN 2-233 Cl F CH₂CH₂OMe CN 2-234 Cl Cl CH₂CH₂OMe CN 2-235 Cl Br CH₂CH₂OMe CN 2-236 Cl I CH₂CH₂OMe CN 2-237 Cl CF₃ CH₂CH₂OMe CN 2-238 Cl CHF₂ CH₂CH₂OMe CN 2-239 Cl CF₂Cl CH₂CH₂OMe CN 2-240 Cl OMe CH₂CH₂OMe CN 2-241 Cl NO₂ CH₂CH₂OMe CN 2-242 Cl SO₂Me CH₂CH₂OMe CN 2-243 OMe Me CH₂CH₂OMe CN 2-244 OMe F CH₂CH₂OMe CN 2-245 OMe Cl CH₂CH₂OMe CN 2-246 OMe Br CH₂CH₂OMe CN 2-247 OMe I CH₂CH₂OMe CN 2-248 OMe CF₃ CH₂CH₂OMe CN 2-249 OMe CHF₂ CH₂CH₂OMe CN 2-250 OMe CF₂Cl CH₂CH₂OMe CN 2-251 OMe OMe CH₂CH₂OMe CN 2-252 OMe NO₂ CH₂CH₂OMe CN 2-253 OMe SO₂Me CH₂CH₂OMe CN 2-254 SO₂Me Me CH₂CH₂OMe CN 2-255 SO₂Me F CH₂CH₂OMe CN 2-256 SO₂Me Cl CH₂CH₂OMe CN 2-257 SO₂Me Br CH₂CH₂OMe CN 2-258 SO₂Me I CH₂CH₂OMe CN 2-259 SO₂Me CF₃ CH₂CH₂OMe CN 2-260 SO₂Me CHF₂ CH₂CH₂OMe CN 2-261 SO₂Me CF₂Cl CH₂CH₂OMe CN 2-262 SO₂Me OMe CH₂CH₂OMe CN 2-263 SO₂Me NO₂ CH₂CH₂OMe CN 2-264 SO₂Me SO₂Me CH₂CH₂OMe CN

TABLE 3 Compounds according to the invention of the formula (I) in which Q is Q3, R^(i) is methyl and R^(h), R^(k) and W are each hydrogen, t = 1 and the other radicals have the meanings indicated in the table

No. X Z R R′ Physical data (¹H NMR) 3-1  Me Me Me H 3-2  Me F Me H 3-3  Me Cl Me H 3-4  Me Br Me H 3-5  Me I Me H 3-6  Me CF₃ Me H 3-7  Me CHF₂ Me H 3-8  Me CF₂Cl Me H 3-9  Me OMe Me H 3-10  Me NO₂ Me H 3-11  Me SO₂Me Me H 3-12  Cl Me Me H 3-13  Cl F Me H 3-14  Cl Cl Me H 3-15  Cl Br Me H 3-16  Cl I Me H 3-17  Cl CF₃ Me H 3-18  Cl CHF₂ Me H 3-19  Cl CF₂Cl Me H 3-20  Cl OMe Me H 3-21  Cl NO₂ Me H 3-22  Cl SO₂Me Me H 3-23  OMe Me Me H 3-24  OMe F Me H 3-25  OMe Cl Me H 3-26  OMe Br Me H 3-27  OMe I Me H 3-28  OMe CF₃ Me H 3-29  OMe CHF₂ Me H 3-30  OMe CF₂Cl Me H 3-31  OMe OMe Me H 3-32  OMe NO₂ Me H 3-33  OMe SO₂Me Me H 3-34  SO₂Me Me Me H 3-35  SO₂Me F Me H 3-36  SO₂Me Cl Me H 3-37  SO₂Me Br Me H 3-38  SO₂Me I Me H 3-39  SO₂Me CF₃ Me H 3-40  SO₂Me CHF₂ Me H 3-41  SO₂Me CF₂Cl Me H 3-42  SO₂Me OMe Me H 3-43  SO₂Me NO₂ Me H 3-44  SO₂Me SO₂Me Me H 3-45  Me Me Et H 3-46  Me F Et H 3-47  Me Cl Et H 3-48  Me Br Et H 3-49  Me I Et H 3-50  Me CF₃ Et H 3-51  Me CHF₂ Et H 3-52  Me CF₂Cl Et H 3-53  Me OMe Et H 3-54  Me NO₂ Et H 3-55  Me SO₂Me Et H 3-56  Cl Me Et H 3-57  Cl F Et H 3-58  Cl Cl Et H 3-59  Cl Br Et H 3-60  Cl I Et H 3-61  Cl CF₃ Et H 3-62  Cl CHF₂ Et H 3-63  Cl CF₂Cl Et H 3-64  Cl OMe Et H 3-65  Cl NO₂ Et H 3-66  Cl SO₂Me Et H 3-67  OMe Me Et H 3-68  OMe F Et H 3-69  OMe Cl Et H 3-70  OMe Br Et H 3-71  OMe I Et H 3-72  OMe CF₃ Et H 3-73  OMe CHF₂ Et H 3-74  OMe CF₂Cl Et H 3-75  OMe OMe Et H 3-76  OMe NO₂ Et H 3-77  OMe SO₂Me Et H 3-78  SO₂Me Me Et H 3-79  SO₂Me F Et H 3-80  SO₂Me Cl Et H 3-81  SO₂Me Br Et H 3-82  SO₂Me I Et H 3-83  SO₂Me CF₃ Et H 3-84  SO₂Me CHF₂ Et H 3-85  SO₂Me CF₂Cl Et H 3-86  SO₂Me OMe Et H 3-87  SO₂Me NO₂ Et H 3-88  SO₂Me SO₂Me Et H 3-89  Me Me CH₂CH₂OMe H 3-90  Me F CH₂CH₂OMe H 3-91  Me Cl CH₂CH₂OMe H 3-92  Me Br CH₂CH₂OMe H 3-93  Me I CH₂CH₂OMe H 3-94  Me CF₃ CH₂CH₂OMe H 3-95  Me CHF₂ CH₂CH₂OMe H 3-96  Me CF₂Cl CH₂CH₂OMe H 3-97  Me OMe CH₂CH₂OMe H 3-98  Me NO₂ CH₂CH₂OMe H 3-99  Me SO₂Me CH₂CH₂OMe H 3-100 Cl Me CH₂CH₂OMe H 3-101 Cl F CH₂CH₂OMe H 3-102 Cl Cl CH₂CH₂OMe H 3-103 Cl Br CH₂CH₂OMe H 3-104 Cl I CH₂CH₂OMe H 3-105 Cl CF₃ CH₂CH₂OMe H 3-106 Cl CHF₂ CH₂CH₂OMe H 3-107 Cl CF₂Cl CH₂CH₂OMe H 3-108 Cl OMe CH₂CH₂OMe H 3-109 Cl NO₂ CH₂CH₂OMe H 3-110 Cl SO₂Me CH₂CH₂OMe H 3-111 OMe Me CH₂CH₂OMe H 3-112 OMe F CH₂CH₂OMe H 3-113 OMe Cl CH₂CH₂OMe H 3-114 OMe Br CH₂CH₂OMe H 3-115 OMe I CH₂CH₂OMe H 3-116 OMe CF₃ CH₂CH₂OMe H 3-117 OMe CHF₂ CH₂CH₂OMe H 3-118 OMe CF₂Cl CH₂CH₂OMe H 3-119 OMe OMe CH₂CH₂OMe H 3-120 OMe NO₂ CH₂CH₂OMe H 3-121 OMe SO₂Me CH₂CH₂OMe H 3-122 SO₂Me Me CH₂CH₂OMe H 3-123 SO₂Me F CH₂CH₂OMe H 3-124 SO₂Me Cl CH₂CH₂OMe H 3-125 SO₂Me Br CH₂CH₂OMe H 3-126 SO₂Me I CH₂CH₂OMe H 3-127 SO₂Me CF₃ CH₂CH₂OMe H 3-128 SO₂Me CHF₂ CH₂CH₂OMe H 3-129 SO₂Me CF₂Cl CH₂CH₂OMe H 3-130 SO₂Me OMe CH₂CH₂OMe H 3-131 SO₂Me NO₂ CH₂CH₂OMe H 3-132 SO₂Me SO₂Me CH₂CH₂OMe H 3-133 Me Me Me CN 3-134 Me F Me CN 3-135 Me Cl Me CN 3-136 Me Br Me CN 3-137 Me I Me CN 3-138 Me CF₃ Me CN 3-139 Me CHF₂ Me CN 3-140 Me CF₂Cl Me CN 3-141 Me OMe Me CN 3-142 Me NO₂ Me CN 3-143 Me SO₂Me Me CN 3-144 Cl Me Me CN 3-145 Cl F Me CN 3-146 Cl Cl Me CN 3-147 Cl Br Me CN 3-148 Cl I Me CN 3-149 Cl CF₃ Me CN 3-150 Cl CHF₂ Me CN 3-151 Cl CF₂Cl Me CN 3-152 Cl OMe Me CN 3-153 Cl NO₂ Me CN 3-154 Cl SO₂Me Me CN 3-155 OMe Me Me CN 3-156 OMe F Me CN 3-157 OMe Cl Me CN 3-158 OMe Br Me CN 3-159 OMe I Me CN 3-160 OMe CF₃ Me CN (400 MHz, CDCl₃ δ, ppm) 7.94 (d, 1H), 7.86 (d, 1H), 7.52 (s, 1H), 3.99 (s, 3H), 3.75 (s, 3H), 3.69 (s, 3H) 3-161 OMe CHF₂ Me CN 3-162 OMe CF₂Cl Me CN 3-163 OMe OMe Me CN 3-164 OMe NO₂ Me CN 3-165 OMe SO₂Me Me CN 3-166 SO₂Me Me Me CN 3-167 SO₂Me F Me CN 3-168 SO₂Me Cl Me CN 3-169 SO₂Me Br Me CN 3-170 SO₂Me I Me CN 3-171 SO₂Me CF₃ Me CN 3-172 SO₂Me CHF₂ Me CN 3-173 SO₂Me CF₂Cl Me CN 3-174 SO₂Me OMe Me CN 3-175 SO₂Me NO₂ Me CN 3-176 SO₂Me SO₂Me Me CN 3-177 Me Me Et CN 3-178 Me F Et CN 3-179 Me Cl Et CN 3-180 Me Br Et CN 3-181 Me I Et CN 3-182 Me CF₃ Et CN 3-183 Me CHF₂ Et CN 3-184 Me CF₂Cl Et CN 3-185 Me OMe Et CN 3-186 Me NO₂ Et CN 3-187 Me SO₂Me Et CN 3-188 Cl Me Et CN 3-189 Cl F Et CN 3-190 Cl Cl Et CN 3-191 Cl Br Et CN 3-192 Cl I Et CN 3-193 Cl CF₃ Et CN 3-194 Cl CHF₂ Et CN 3-195 Cl CF₂Cl Et CN 3-196 Cl OMe Et CN 3-197 Cl NO₂ Et CN 3-198 Cl SO₂Me Et CN 3-199 OMe Me Et CN 3-200 OMe F Et CN 3-201 OMe Cl Et CN 3-202 OMe Br Et CN 3-203 OMe I Et CN 3-204 OMe CF₃ Et CN 3-205 OMe CHF₂ Et CN 3-206 OMe CF₂Cl Et CN 3-207 OMe OMe Et CN 3-208 OMe NO₂ Et CN 3-209 OMe SO₂Me Et CN 3-210 SO₂Me Me Et CN 3-211 SO₂Me F Et CN 3-212 SO₂Me Cl Et CN 3-213 SO₂Me Br Et CN 3-214 SO₂Me I Et CN 3-215 SO₂Me CF₃ Et CN 3-216 SO₂Me CHF₂ Et CN 3-217 SO₂Me CF₂Cl Et CN 3-218 SO₂Me OMe Et CN 3-219 SO₂Me NO₂ Et CN 3-220 SO₂Me SO₂Me Et CN 3-221 Me Me CH₂CH₂OMe CN 3-222 Me F CH₂CH₂OMe CN 3-223 Me Cl CH₂CH₂OMe CN 3-224 Me Br CH₂CH₂OMe CN 3-225 Me I CH₂CH₂OMe CN 3-226 Me CF₃ CH₂CH₂OMe CN 3-227 Me CHF₂ CH₂CH₂OMe CN 3-228 Me CF₂Cl CH₂CH₂OMe CN 3-229 Me OMe CH₂CH₂OMe CN 3-230 Me NO₂ CH₂CH₂OMe CN 3-231 Me SO₂Me CH₂CH₂OMe CN 3-232 Cl Me CH₂CH₂OMe CN 3-233 Cl F CH₂CH₂OMe CN 3-234 Cl Cl CH₂CH₂OMe CN 3-235 Cl Br CH₂CH₂OMe CN 3-236 Cl I CH₂CH₂OMe CN 3-237 Cl CF₃ CH₂CH₂OMe CN 3-238 Cl CHF₂ CH₂CH₂OMe CN 3-239 Cl CF₂Cl CH₂CH₂OMe CN 3-240 Cl OMe CH₂CH₂OMe CN 3-241 Cl NO₂ CH₂CH₂OMe CN 3-242 Cl SO₂Me CH₂CH₂OMe CN 3-243 OMe Me CH₂CH₂OMe CN 3-244 OMe F CH₂CH₂OMe CN 3-245 OMe Cl CH₂CH₂OMe CN 3-246 OMe Br CH₂CH₂OMe CN 3-247 OMe I CH₂CH₂OMe CN 3-248 OMe CF₃ CH₂CH₂OMe CN 3-249 OMe CHF₂ CH₂CH₂OMe CN 3-250 OMe CF₂Cl CH₂CH₂OMe CN 3-251 OMe OMe CH₂CH₂OMe CN 3-252 OMe NO₂ CH₂CH₂OMe CN 3-253 OMe SO₂Me CH₂CH₂OMe CN 3-254 SO₂Me Me CH₂CH₂OMe CN 3-255 SO₂Me F CH₂CH₂OMe CN 3-256 SO₂Me Cl CH₂CH₂OMe CN 3-257 SO₂Me Br CH₂CH₂OMe CN 3-258 SO₂Me I CH₂CH₂OMe CN 3-259 SO₂Me CF₃ CH₂CH₂OMe CN 3-260 SO₂Me CHF₂ CH₂CH₂OMe CN 3-261 SO₂Me CF₂Cl CH₂CH₂OMe CN 3-262 SO₂Me OMe CH₂CH₂OMe CN 3-263 SO₂Me NO₂ CH₂CH₂OMe CN 3-264 SO₂Me SO₂Me CH₂CH₂OMe CN

TABLE 3a Compounds according to the invention of the formula (I) in which Q is Q3, R^(i) is ethyl and R^(h), R^(k) and W are each hydrogen, t = 1 and the other radicals have the meanings indicated in the table

No. X Z R R′ Physical data (¹H NMR) 3a-1  Me Me Me H 3a-2  Me F Me H 3a-3  Me Cl Me H 3a-4  Me Br Me H 3a-5  Me I Me H 3a-6  Me CF₃ Me H 3a-7  Me CHF₂ Me H 3a-8  Me CF₂Cl Me H 3a-9  Me OMe Me H 3a-10  Me NO₂ Me H 3a-11  Me SO₂Me Me H 3a-12  Cl Me Me H 3a-13  Cl F Me H 3a-14  Cl Cl Me H 3a-15  Cl Br Me H 3a-16  Cl I Me H 3a-17  Cl CF₃ Me H 3a-18  Cl CHF₂ Me H 3a-19  Cl CF₂Cl Me H 3a-20  Cl OMe Me H 3a-21  Cl NO₂ Me H 3a-22  Cl SO₂Me Me H 3a-23  OMe Me Me H 3a-24  OMe F Me H 3a-25  OMe Cl Me H 3a-26  OMe Br Me H 3a-27  OMe I Me H 3a-28  OMe CF₃ Me H 3a-29  OMe CHF₂ Me H 3a-30  OMe CF₂Cl Me H 3a-31  OMe OMe Me H 3a-32  OMe NO₂ Me H 3a-33  OMe SO₂Me Me H 3a-34  SO₂Me Me Me H 3a-35  SO₂Me F Me H 3a-36  SO₂Me Cl Me H 3a-37  SO₂Me Br Me H 3a-38  SO₂Me I Me H 3a-39  SO₂Me CF₃ Me H 3a-40  SO₂Me CHF₂ Me H 3a-41  SO₂Me CF₂Cl Me H 3a-42  SO₂Me OMe Me H 3a-43  SO₂Me NO₂ Me H 3a-44  SO₂Me SO₂Me Me H 3a-45  Me Me Et H 3a-46  Me F Et H 3a-47  Me Cl Et H 3a-48  Me Br Et H 3a-49  Me I Et H 3a-50  Me CF₃ Et H 3a-51  Me CHF₂ Et H 3a-52  Me CF₂Cl Et H 3a-53  Me OMe Et H 3a-54  Me NO₂ Et H 3a-55  Me SO₂Me Et H 3a-56  Cl Me Et H 3a-57  Cl F Et H 3a-58  Cl Cl Et H 3a-59  Cl Br Et H 3a-60  Cl I Et H 3a-61  Cl CF₃ Et H 3a-62  Cl CHF₂ Et H 3a-63  Cl CF₂Cl Et H 3a-64  Cl OMe Et H 3a-65  Cl NO₂ Et H 3a-66  Cl SO₂Me Et H 3a-67  OMe Me Et H 3a-68  OMe F Et H 3a-69  OMe Cl Et H 3a-70  OMe Br Et H 3a-71  OMe I Et H 3a-72  OMe CF₃ Et H 3a-73  OMe CHF₂ Et H 3a-74  OMe CF₂Cl Et H 3a-75  OMe OMe Et H 3a-76  OMe NO₂ Et H 3a-77  OMe SO₂Me Et H 3a-78  SO₂Me Me Et H 3a-79  SO₂Me F Et H 3a-80  SO₂Me Cl Et H 3a-81  SO₂Me Br Et H 3a-82  SO₂Me I Et H 3a-83  SO₂Me CF₃ Et H 3a-84  SO₂Me CHF₂ Et H 3a-85  SO₂Me CF₂Cl Et H 3a-86  SO₂Me OMe Et H 3a-87  SO₂Me NO₂ Et H 3a-88  SO₂Me SO₂Me Et H 3a-89  Me Me CH₂CH₂OMe H 3a-90  Me F CH₂CH₂OMe H 3a-91  Me Cl CH₂CH₂OMe H 3a-92  Me Br CH₂CH₂OMe H 3a-93  Me I CH₂CH₂OMe H 3a-94  Me CF₃ CH₂CH₂OMe H 3a-95  Me CHF₂ CH₂CH₂OMe H 3a-96  Me CF₂Cl CH₂CH₂OMe H 3a-97  Me OMe CH₂CH₂OMe H 3a-98  Me NO₂ CH₂CH₂OMe H 3a-99  Me SO₂Me CH₂CH₂OMe H 3a-100 Cl Me CH₂CH₂OMe H 3a-101 Cl F CH₂CH₂OMe H 3a-102 Cl Cl CH₂CH₂OMe H 3a-103 Cl Br CH₂CH₂OMe H 3a-104 Cl I CH₂CH₂OMe H 3a-105 Cl CF₃ CH₂CH₂OMe H 3a-106 Cl CHF₂ CH₂CH₂OMe H 3a-107 Cl CF₂Cl CH₂CH₂OMe H 3a-108 Cl OMe CH₂CH₂OMe H 3a-109 Cl NO₂ CH₂CH₂OMe H 3a-110 Cl SO₂Me CH₂CH₂OMe H 3a-111 OMe Me CH₂CH₂OMe H 3a-112 OMe F CH₂CH₂OMe H 3a-113 OMe Cl CH₂CH₂OMe H 3a-114 OMe Br CH₂CH₂OMe H 3a-115 OMe I CH₂CH₂OMe H 3a-116 OMe CF₃ CH₂CH₂OMe H 3a-117 OMe CHF₂ CH₂CH₂OMe H 3a-118 OMe CF₂Cl CH₂CH₂OMe H 3a-119 OMe OMe CH₂CH₂OMe H 3a-120 OMe NO₂ CH₂CH₂OMe H 3a-121 OMe SO₂Me CH₂CH₂OMe H 3a-122 SO₂Me Me CH₂CH₂OMe H 3a-123 SO₂Me F CH₂CH₂OMe H 3a-124 SO₂Me Cl CH₂CH₂OMe H 3a-125 SO₂Me Br CH₂CH₂OMe H 3a-126 SO₂Me I CH₂CH₂OMe H 3a-127 SO₂Me CF₃ CH₂CH₂OMe H 3a-128 SO₂Me CHF₂ CH₂CH₂OMe H 3a-129 SO₂Me CF₂Cl CH₂CH₂OMe H 3a-130 SO₂Me OMe CH₂CH₂OMe H 3a-131 SO₂Me NO₂ CH₂CH₂OMe H 3a-132 SO₂Me SO₂Me CH₂CH₂OMe H 3a-133 Me Me Me CN 3a-134 Me F Me CN 3a-135 Me Cl Me CN 3a-136 Me Br Me CN 3a-137 Me I Me CN 3a-138 Me CF₃ Me CN 3a-139 Me CHF₂ Me CN 3a-140 Me CF₂Cl Me CN 3a-141 Me OMe Me CN 3a-142 Me NO₂ Me CN 3a-143 Me SO₂Me Me CN 3a-144 Cl Me Me CN 3a-145 Cl F Me CN 3a-146 Cl Cl Me CN 3a-147 Cl Br Me CN 3a-148 Cl I Me CN 3a-149 Cl CF₃ Me CN 3a-150 Cl CHF₂ Me CN 3a-151 Cl CF₂Cl Me CN 3a-152 Cl OMe Me CN 3a-153 Cl NO₂ Me CN 3a-154 Cl SO₂Me Me CN 3a-155 OMe Me Me CN 3a-156 OMe F Me CN 3a-157 OMe Cl Me CN 3a-158 OMe Br Me CN 3a-159 OMe I Me CN 3a-160 OMe CF₃ Me CN 3a-161 OMe CHF₂ Me CN 3a-162 OMe CF₂Cl Me CN 3a-163 OMe OMe Me CN 3a-164 OMe NO₂ Me CN 3a-165 OMe SO₂Me Me CN 3a-166 SO₂Me Me Me CN 3a-167 SO₂Me F Me CN 3a-168 SO₂Me Cl Me CN 3a-169 SO₂Me Br Me CN 3a-170 SO₂Me I Me CN 3a-171 SO₂Me CF₃ Me CN 3a-172 SO₂Me CHF₂ Me CN 3a-173 SO₂Me CF₂Cl Me CN 3a-174 SO₂Me OMe Me CN 3a-175 SO₂Me NO₂ Me CN 3a-176 SO₂Me SO₂Me Me CN 3a-177 Me Me Et CN 3a-178 Me F Et CN 3a-179 Me Cl Et CN 3a-180 Me Br Et CN 3a-181 Me I Et CN 3a-182 Me CF₃ Et CN 3a-183 Me CHF₂ Et CN 3a-184 Me CF₂Cl Et CN 3a-185 Me OMe Et CN 3a-186 Me NO₂ Et CN 3a-187 Me SO₂Me Et CN 3a-188 Cl Me Et CN 3a-189 Cl F Et CN 3a-190 Cl Cl Et CN 3a-191 Cl Br Et CN 3a-192 Cl I Et CN 3a-193 Cl CF₃ Et CN 3a-194 Cl CHF₂ Et CN 3a-195 Cl CF₂Cl Et CN 3a-196 Cl OMe Et CN 3a-197 Cl NO₂ Et CN 3a-198 Cl SO₂Me Et CN 3a-199 OMe Me Et CN 3a-200 OMe F Et CN 3a-201 OMe Cl Et CN 3a-202 OMe Br Et CN 3a-203 OMe I Et CN 3a-204 OMe CF₃ Et CN 3a-205 OMe CHF₂ Et CN 3a-206 OMe CF₂Cl Et CN 3a-207 OMe OMe Et CN 3a-208 OMe NO₂ Et CN 3a-209 OMe SO₂Me Et CN 3a-210 SO₂Me Me Et CN 3a-211 SO₂Me F Et CN 3a-212 SO₂Me Cl Et CN 3a-213 SO₂Me Br Et CN 3a-214 SO₂Me I Et CN 3a-215 SO₂Me CF₃ Et CN 3a-216 SO₂Me CHF₂ Et CN 3a-217 SO₂Me CF₂Cl Et CN 3a-218 SO₂Me OMe Et CN 3a-219 SO₂Me NO₂ Et CN 3a-220 SO₂Me SO₂Me Et CN 3a-221 Me Me CH₂CH₂OMe CN 3a-222 Me F CH₂CH₂OMe CN 3a-223 Me Cl CH₂CH₂OMe CN 3a-224 Me Br CH₂CH₂OMe CN 3a-225 Me I CH₂CH₂OMe CN 3a-226 Me CF₃ CH₂CH₂OMe CN 3a-227 Me CHF₂ CH₂CH₂OMe CN 3a-228 Me CF₂Cl CH₂CH₂OMe CN 3a-229 Me OMe CH₂CH₂OMe CN 3a-230 Me NO₂ CH₂CH₂OMe CN 3a-231 Me SO₂Me CH₂CH₂OMe CN 3a-232 Cl Me CH₂CH₂OMe CN 3a-233 Cl F CH₂CH₂OMe CN 3a-234 Cl Cl CH₂CH₂OMe CN 3a-235 Cl Br CH₂CH₂OMe CN 3a-236 Cl I CH₂CH₂OMe CN 3a-237 Cl CF₃ CH₂CH₂OMe CN 3a-238 Cl CHF₂ CH₂CH₂OMe CN 3a-239 Cl CF₂Cl CH₂CH₂OMe CN 3a-240 Cl OMe CH₂CH₂OMe CN 3a-241 Cl NO₂ CH₂CH₂OMe CN 3a-242 Cl SO₂Me CH₂CH₂OMe CN 3a-243 OMe Me CH₂CH₂OMe CN 3a-244 OMe F CH₂CH₂OMe CN 3a-245 OMe Cl CH₂CH₂OMe CN 3a-246 OMe Br CH₂CH₂OMe CN 3a-247 OMe I CH₂CH₂OMe CN 3a-248 OMe CF₃ CH₂CH₂OMe CN 3a-249 OMe CHF₂ CH₂CH₂OMe CN 3a-250 OMe CF₂Cl CH₂CH₂OMe CN 3a-251 OMe OMe CH₂CH₂OMe CN 3a-252 OMe NO₂ CH₂CH₂OMe CN 3a-253 OMe SO₂Me CH₂CH₂OMe CN 3a-254 SO₂Me Me CH₂CH₂OMe CN 3a-255 SO₂Me F CH₂CH₂OMe CN 3a-256 SO₂Me Cl CH₂CH₂OMe CN 3a-257 SO₂Me Br CH₂CH₂OMe CN 3a-258 SO₂Me I CH₂CH₂OMe CN 3a-259 SO₂Me CF₃ CH₂CH₂OMe CN 3a-260 SO₂Me CHF₂ CH₂CH₂OMe CN 3a-261 SO₂Me CF₂Cl CH₂CH₂OMe CN 3a-262 SO₂Me OMe CH₂CH₂OMe CN 3a-263 SO₂Me NO₂ CH₂CH₂OMe CN 3a-264 SO₂Me SO₂Me CH₂CH₂OMe CN

TABLE 4 Compounds according to the invention of the formula (I) in which Q is Q3, R^(i) and R^(k) are each methyl, R^(h) and W are each hydrogen, t = 1 and the other radicals have the meanings indicated in the table

No. X Z R R′ Physical data (1H NMR) 4-1  Me Me Me H 4-2  Me F Me H 4-3  Me Cl Me H 4-4  Me Br Me H 4-5  Me I Me H 4-6  Me CF₃ Me H 4-7  Me CHF₂ Me H 4-8  Me CF₂Cl Me H 4-9  Me OMe Me H 4-10  Me NO₂ Me H 4-11  Me SO₂Me Me H 4-12  Cl Me Me H 4-13  Cl F Me H 4-14  Cl Cl Me H 4-15  Cl Br Me H 4-16  Cl I Me H 4-17  Cl CF₃ Me H 4-18  Cl CHF₂ Me H 4-19  Cl CF₂Cl Me H 4-20  Cl OMe Me H 4-21  Cl NO₂ Me H 4-22  Cl SO₂Me Me H 4-23  OMe Me Me H 4-24  OMe F Me H 4-25  OMe Cl Me H 4-26  OMe Br Me H 4-27  OMe I Me H 4-28  OMe CF₃ Me H 4-29  OMe CHF₂ Me H 4-30  OMe CF₂Cl Me H 4-31  OMe OMe Me H 4-32  OMe NO₂ Me H 4-33  OMe SO₂Me Me H 4-34  SO₂Me Me Me H 4-35  SO₂Me F Me H 4-36  SO₂Me Cl Me H 4-37  SO₂Me Br Me H 4-38  SO₂Me I Me H 4-39  SO₂Me CF₃ Me H 4-40  SO₂Me CHF₂ Me H 4-41  SO₂Me CF₂Cl Me H 4-42  SO₂Me OMe Me H 4-43  SO₂Me NO₂ Me H 4-44  SO₂Me SO₂Me Me H 4-45  Me Me Et H 4-46  Me F Et H 4-47  Me Cl Et H 4-48  Me Br Et H 4-49  Me I Et H 4-50  Me CF₃ Et H 4-51  Me CHF₂ Et H 4-52  Me CF₂Cl Et H 4-53  Me OMe Et H 4-54  Me NO₂ Et H 4-55  Me SO₂Me Et H 4-56  Cl Me Et H 4-57  Cl F Et H 4-58  Cl Cl Et H 4-59  Cl Br Et H 4-60  Cl I Et H 4-61  Cl CF₃ Et H 4-62  Cl CHF₂ Et H 4-63  Cl CF₂Cl Et H 4-64  Cl OMe Et H 4-65  Cl NO₂ Et H 4-66  Cl SO₂Me Et H 4-67  OMe Me Et H 4-68  OMe F Et H 4-69  OMe Cl Et H 4-70  OMe Br Et H 4-71  OMe I Et H 4-72  OMe CF₃ Et H 4-73  OMe CHF₂ Et H 4-74  OMe CF₂Cl Et H 4-75  OMe OMe Et H 4-76  OMe NO₂ Et H 4-77  OMe SO₂Me Et H 4-78  SO₂Me Me Et H 4-79  SO₂Me F Et H 4-80  SO₂Me Cl Et H 4-81  SO₂Me Br Et H 4-82  SO₂Me I Et H 4-83  SO₂Me CF₃ Et H 4-84  SO₂Me CHF₂ Et H 4-85  SO₂Me CF₂Cl Et H 4-86  SO₂Me OMe Et H 4-87  SO₂Me NO₂ Et H 4-88  SO₂Me SO₂Me Et H 4-89  Me Me CH₂CH₂OMe H 4-90  Me F CH₂CH₂OMe H 4-91  Me Cl CH₂CH₂OMe H 4-92  Me Br CH₂CH₂OMe H 4-93  Me I CH₂CH₂OMe H 4-94  Me CF₃ CH₂CH₂OMe H 4-95  Me CHF₂ CH₂CH₂OMe H 4-96  Me CF₂Cl CH₂CH₂OMe H 4-97  Me OMe CH₂CH₂OMe H 4-98  Me NO₂ CH₂CH₂OMe H 4-99  Me SO₂Me CH₂CH₂OMe H 4-100 Cl Me CH₂CH₂OMe H 4-101 Cl F CH₂CH₂OMe H 4-102 Cl Cl CH₂CH₂OMe H 4-103 Cl Br CH₂CH₂OMe H 4-104 Cl I CH₂CH₂OMe H 4-105 Cl CF₃ CH₂CH₂OMe H 4-106 Cl CHF₂ CH₂CH₂OMe H 4-107 Cl CF₂Cl CH₂CH₂OMe H 4-108 Cl OMe CH₂CH₂OMe H 4-109 Cl NO₂ CH₂CH₂OMe H 4-110 Cl SO₂Me CH₂CH₂OMe H 4-111 OMe Me CH₂CH₂OMe H 4-112 OMe F CH₂CH₂OMe H 4-113 OMe Cl CH₂CH₂OMe H 4-114 OMe Br CH₂CH₂OMe H 4-115 OMe I CH₂CH₂OMe H 4-116 OMe CF₃ CH₂CH₂OMe H 4-117 OMe CHF₂ CH₂CH₂OMe H 4-118 OMe CF₂Cl CH₂CH₂OMe H 4-119 OMe OMe CH₂CH₂OMe H 4-120 OMe NO₂ CH₂CH₂OMe H 4-121 OMe SO₂Me CH₂CH₂OMe H 4-122 SO₂Me Me CH₂CH₂OMe H 4-123 SO₂Me F CH₂CH₂OMe H 4-124 SO₂Me Cl CH₂CH₂OMe H 4-125 SO₂Me Br CH₂CH₂OMe H 4-126 SO₂Me I CH₂CH₂OMe H 4-127 SO₂Me CF₃ CH₂CH₂OMe H 4-128 SO₂Me CHF₂ CH₂CH₂OMe H 4-129 SO₂Me CF₂Cl CH₂CH₂OMe H 4-130 SO₂Me OMe CH₂CH₂OMe H 4-131 SO₂Me NO₂ CH₂CH₂OMe H 4-132 SO₂Me SO₂Me CH₂CH₂OMe H 4-133 Me Me Me CN 4-134 Me F Me CN 4-135 Me Cl Me CN 4-136 Me Br Me CN 4-137 Me I Me CN 4-138 Me CF₃ Me CN 4-139 Me CHF₂ Me CN 4-140 Me CF₂Cl Me CN 4-141 Me OMe Me CN 4-142 Me NO₂ Me CN 4-143 Me SO₂Me Me CN 4-144 Cl Me Me CN 4-145 Cl F Me CN 4-146 Cl Cl Me CN 4-147 Cl Br Me CN 4-148 Cl I Me CN 4-149 Cl CF₃ Me CN 4-150 Cl CHF₂ Me CN 4-151 Cl CF₂Cl Me CN 4-152 Cl OMe Me CN 4-153 Cl NO₂ Me CN 4-154 Cl SO₂Me Me CN 4-155 OMe Me Me CN 4-156 OMe F Me CN 4-157 OMe Cl Me CN 4-158 OMe Br Me CN 4-159 OMe I Me CN 4-160 OMe CF₃ Me CN (400 MHz, CDCl₃ δ, ppm) 7.85 (d, 1H), 7.75 (d, 1H), 4.03 (s, 3H), 3.68 (s, 3H), 3.65 (s, 3H), 1.90 (s, 3H) 4-161 OMe CHF₂ Me CN 4-162 OMe CF₂Cl Me CN 4-163 OMe OMe Me CN 4-164 OMe NO₂ Me CN 4-165 OMe SO₂Me Me CN 4-166 SO₂Me Me Me CN 4-167 SO₂Me F Me CN 4-168 SO₂Me Cl Me CN 4-169 SO₂Me Br Me CN 4-170 SO₂Me I Me CN 4-171 SO₂Me CF₃ Me CN 4-172 SO₂Me CHF₂ Me CN 4-173 SO₂Me CF₂Cl Me CN 4-174 SO₂Me OMe Me CN 4-175 SO₂Me NO₂ Me CN 4-176 SO₂Me SO₂Me Me CN 4-177 Me Me Et CN 4-178 Me F Et CN 4-179 Me Cl Et CN 4-180 Me Br Et CN 4-181 Me I Et CN 4-182 Me CF₃ Et CN 4-183 Me CHF₂ Et CN 4-184 Me CF₂Cl Et CN 4-185 Me OMe Et CN 4-186 Me NO₂ Et CN 4-187 Me SO₂Me Et CN 4-188 Cl Me Et CN 4-189 Cl F Et CN 4-190 Cl Cl Et CN 4-191 Cl Br Et CN 4-192 Cl I Et CN 4-193 Cl CF₃ Et CN 4-194 Cl CHF₂ Et CN 4-195 Cl CF₂Cl Et CN 4-196 Cl OMe Et CN 4-197 Cl NO₂ Et CN 4-198 Cl SO₂Me Et CN 4-199 OMe Me Et CN 4-200 OMe F Et CN 4-201 OMe Cl Et CN 4-202 OMe Br Et CN 4-203 OMe I Et CN 4-204 OMe CF₃ Et CN 4-205 OMe CHF₂ Et CN 4-206 OMe CF₂Cl Et CN 4-207 OMe OMe Et CN 4-208 OMe NO₂ Et CN 4-209 OMe SO₂Me Et CN 4-210 SO₂Me Me Et CN 4-211 SO₂Me F Et CN 4-212 SO₂Me Cl Et CN 4-213 SO₂Me Br Et CN 4-214 SO₂Me I Et CN 4-215 SO₂Me CF₃ Et CN 4-216 SO₂Me CHF₂ Et CN 4-217 SO₂Me CF₂Cl Et CN 4-218 SO₂Me OMe Et CN 4-219 SO₂Me NO₂ Et CN 4-220 SO₂Me SO₂Me Et CN 4-221 Me Me CH₂CH₂OMe CN 4-222 Me F CH₂CH₂OMe CN 4-223 Me Cl CH₂CH₂OMe CN 4-224 Me Br CH₂CH₂OMe CN 4-225 Me I CH₂CH₂OMe CN 4-226 Me CF₃ CH₂CH₂OMe CN 4-227 Me CHF₂ CH₂CH₂OMe CN 4-228 Me CF₂Cl CH₂CH₂OMe CN 4-229 Me OMe CH₂CH₂OMe CN 4-230 Me NO₂ CH₂CH₂OMe CN 4-231 Me SO₂Me CH₂CH₂OMe CN 4-232 Cl Me CH₂CH₂OMe CN 4-233 Cl F CH₂CH₂OMe CN 4-234 Cl Cl CH₂CH₂OMe CN 4-235 Cl Br CH₂CH₂OMe CN 4-236 Cl I CH₂CH₂OMe CN 4-237 Cl CF₃ CH₂CH₂OMe CN 4-238 Cl CHF₂ CH₂CH₂OMe CN 4-239 Cl CF₂Cl CH₂CH₂OMe CN 4-240 Cl OMe CH₂CH₂OMe CN 4-241 Cl NO₂ CH₂CH₂OMe CN 4-242 Cl SO₂Me CH₂CH₂OMe CN 4-243 OMe Me CH₂CH₂OMe CN 4-244 OMe F CH₂CH₂OMe CN 4-245 OMe Cl CH₂CH₂OMe CN 4-246 OMe Br CH₂CH₂OMe CN 4-247 OMe I CH₂CH₂OMe CN 4-248 OMe CF₃ CH₂CH₂OMe CN 4-249 OMe CHF₂ CH₂CH₂OMe CN 4-250 OMe CF₂Cl CH₂CH₂OMe CN 4-251 OMe OMe CH₂CH₂OMe CN 4-252 OMe NO₂ CH₂CH₂OMe CN 4-253 OMe SO₂Me CH₂CH₂OMe CN 4-254 SO₂Me Me CH₂CH₂OMe CN 4-255 SO₂Me F CH₂CH₂OMe CN 4-256 SO₂Me Cl CH₂CH₂OMe CN 4-257 SO₂Me Br CH₂CH₂OMe CN 4-258 SO₂Me I CH₂CH₂OMe CN 4-259 SO₂Me CF₃ CH₂CH₂OMe CN 4-260 SO₂Me CHF₂ CH₂CH₂OMe CN 4-261 SO₂Me CF₂Cl CH₂CH₂OMe CN 4-262 SO₂Me OMe CH₂CH₂OMe CN 4-263 SO₂Me NO₂ CH₂CH₂OMe CN 4-264 SO₂Me SO₂Me CH₂CH₂OMe CN

TABLE 5 Compounds according to the invention of the formula (I) in which Q is Q4, W is hydrogen, t = 1 and the other radicals have the meanings indicated in the table

No. X Z R R′ Physical data (1H NMR) 5-1 Me Me Me H 5-2 Me F Me H 5-3 Me Cl Me H 5-4 Me Br Me H 5-5 Me I Me H 5-6 Me CF₃ Me H 5-7 Me CHF₂ Me H 5-8 Me CF₂Cl Me H 5-9 Me OMe Me H 5-10 Me NO₂ Me H 5-11 Me SO₂Me Me H 5-12 Cl Me Me H 5-13 Cl F Me H 5-14 Cl Cl Me H 5-15 Cl Br Me H 5-16 Cl I Me H 5-17 Cl CF₃ Me H 5-18 Cl CHF₂ Me H 5-19 Cl CF₂Cl Me H 5-20 Cl OMe Me H 5-21 Cl NO₂ Me H 5-22 Cl SO₂Me Me H 5-23 OMe Me Me H 5-24 OMe F Me H 5-25 OMe Cl Me H 5-26 OMe Br Me H 5-27 OMe I Me H 5-28 OMe CF₃ Me H 5-29 OMe CHF₂ Me H 5-30 OMe CF₂Cl Me H 5-31 OMe OMe Me H 5-32 OMe NO₂ Me H 5-33 OMe SO₂Me Me H 5-34 SO₂Me Me Me H 5-35 SO₂Me F Me H 5-36 SO₂Me Cl Me H 5-37 SO₂Me Br Me H 5-38 SO₂Me I Me H 5-39 SO₂Me CF₃ Me H 5-40 SO₂Me CHF₂ Me H 5-41 SO₂Me CF₂Cl Me H 5-42 SO₂Me OMe Me H 5-43 SO₂Me NO₂ Me H 5-44 SO₂Me SO₂Me Me H 5-45 Me Me Et H 5-46 Me F Et H 5-47 Me Cl Et H 5-48 Me Br Et H 5-49 Me I Et H 5-50 Me CF₃ Et H 5-51 Me CHF₂ Et H 5-52 Me CF₂Cl Et H 5-53 Me OMe Et H 5-54 Me NO₂ Et H 5-55 Me SO₂Me Et H 5-56 Cl Me Et H 5-57 Cl F Et H 5-58 Cl Cl Et H 5-59 Cl Br Et H 5-60 Cl I Et H 5-61 Cl CF₃ Et H 5-62 Cl CHF₂ Et H 5-63 Cl CF₂Cl Et H 5-64 Cl OMe Et H 5-65 Cl NO₂ Et H 5-66 Cl SO₂Me Et H 5-67 OMe Me Et H 5-68 OMe F Et H 5-69 OMe Cl Et H 5-70 OMe Br Et H 5-71 OMe I Et H 5-72 OMe CF₃ Et H 5-73 OMe CHF₂ Et H 5-74 OMe CF₂Cl Et H 5-75 OMe OMe Et H 5-76 OMe NO₂ Et H 5-77 OMe SO₂Me Et H 5-78 SO₂Me Me Et H 5-79 SO₂Me F Et H 5-80 SO₂Me Cl Et H 5-81 SO₂Me Br Et H 5-82 SO₂Me I Et H 5-83 SO₂Me CF₃ Et H 5-84 SO₂Me CHF₂ Et H 5-85 SO₂Me CF₂Cl Et H 5-86 SO₂Me OMe Et H 5-87 SO₂Me NO₂ Et H 5-88 SO₂Me SO₂Me Et H 5-89 Me Me CH₂CH₂OMe H 5-90 Me F CH₂CH₂OMe H 5-91 Me Cl CH₂CH₂OMe H 5-92 Me Br CH₂CH₂OMe H 5-93 Me I CH₂CH₂OMe H 5-94 Me CF₃ CH₂CH₂OMe H 5-95 Me CHF₂ CH₂CH₂OMe H 5-96 Me CF₂Cl CH₂CH₂OMe H 5-97 Me OMe CH₂CH₂OMe H 5-98 Me NO₂ CH₂CH₂OMe H 5-99 Me SO₂Me CH₂CH₂OMe H 5-100 Cl Me CH₂CH₂OMe H 5-101 Cl F CH₂CH₂OMe H 5-102 Cl Cl CH₂CH₂OMe H 5-103 Cl Br CH₂CH₂OMe H 5-104 Cl I CH₂CH₂OMe H 5-105 Cl CF₃ CH₂CH₂OMe H 5-106 Cl CHF₂ CH₂CH₂OMe H 5-107 Cl CF₂Cl CH₂CH₂OMe H 5-108 Cl OMe CH₂CH₂OMe H 5-109 Cl NO₂ CH₂CH₂OMe H 5-110 Cl SO₂Me CH₂CH₂OMe H 5-111 OMe Me CH₂CH₂OMe H 5-112 OMe F CH₂CH₂OMe H 5-113 OMe Cl CH₂CH₂OMe H 5-114 OMe Br CH₂CH₂OMe H 5-115 OMe I CH₂CH₂OMe H 5-116 OMe CF₃ CH₂CH₂OMe H 5-117 OMe CHF₂ CH₂CH₂OMe H 5-118 OMe CF₂Cl CH₂CH₂OMe H 5-119 OMe OMe CH₂CH₂OMe H 5-120 OMe NO₂ CH₂CH₂OMe H 5-121 OMe SO₂Me CH₂CH₂OMe H 5-122 SO₂Me Me CH₂CH₂OMe H 5-123 SO₂Me F CH₂CH₂OMe H 5-124 SO₂Me Cl CH₂CH₂OMe H 5-125 SO₂Me Br CH₂CH₂OMe H 5-126 SO₂Me I CH₂CH₂OMe H 5-127 SO₂Me CF₃ CH₂CH₂OMe H 5-128 SO₂Me CHF₂ CH₂CH₂OMe H 5-129 SO₂Me CF₂Cl CH₂CH₂OMe H 5-130 SO₂Me OMe CH₂CH₂OMe H 5-131 SO₂Me NO₂ CH₂CH₂OMe H 5-132 SO₂Me SO₂Me CH₂CH₂OMe H 5-133 Me Me Me CN 5-134 Me F Me CN 5-135 Me Cl Me CN 5-136 Me Br Me CN 5-137 Me I Me CN 5-138 Me CF₃ Me CN 5-139 Me CHF₂ Me CN 5-140 Me CF₂Cl Me CN 5-141 Me OMe Me CN 5-142 Me NO₂ Me CN 5-143 Me SO₂Me Me CN 5-144 Cl Me Me CN 5-145 Cl F Me CN 5-146 Cl Cl Me CN 5-147 Cl Br Me CN 5-148 Cl I Me CN 5-149 Cl CF₃ Me CN 5-150 Cl CHF₂ Me CN 5-151 Cl CF₂Cl Me CN 5-152 Cl OMe Me CN 5-153 Cl NO₂ Me CN 5-154 Cl SO₂Me Me CN 5-155 OMe Me Me CN 5-156 OMe F Me CN 5-157 OMe Cl Me CN 5-158 OMe Br Me CN 5-159 OMe I Me CN 5-160 OMe CF₃ Me CN 5-161 OMe CHF₂ Me CN 5-162 OMe CF₂Cl Me CN 5-163 OMe OMe Me CN 5-164 OMe NO₂ Me CN 5-165 OMe SO₂Me Me CN 5-166 SO₂Me Me Me CN 5-167 SO₂Me F Me CN 5-168 SO₂Me Cl Me CN 5-169 SO₂Me Br Me CN 5-170 SO₂Me I Me CN 5-171 SO₂Me CF₃ Me CN 5-172 SO₂Me CHF₂ Me CN 5-173 SO₂Me CF₂Cl Me CN 5-174 SO₂Me OMe Me CN 5-175 SO₂Me NO₂ Me CN 5-176 SO₂Me SO₂Me Me CN 5-177 Me Me Et CN 5-178 Me F Et CN 5-179 Me Cl Et CN 5-180 Me Br Et CN 5-181 Me I Et CN 5-182 Me CF₃ Et CN 5-183 Me CHF₂ Et CN 5-184 Me CF₂Cl Et CN 5-185 Me OMe Et CN 5-186 Me NO₂ Et CN 5-187 Me SO₂Me Et CN 5-188 Cl Me Et CN 5-189 Cl F Et CN 5-190 Cl Cl Et CN 5-191 Cl Br Et CN 5-192 Cl I Et CN 5-193 Cl CF₃ Et CN 5-194 Cl CHF₂ Et CN 5-195 Cl CF₂Cl Et CN 5-196 Cl OMe Et CN 5-197 Cl NO₂ Et CN 5-198 Cl SO₂Me Et CN 5-199 OMe Me Et CN 5-200 OMe F Et CN 5-201 OMe Cl Et CN 5-202 OMe Br Et CN 5-203 OMe I Et CN 5-204 OMe CF₃ Et CN 5-205 OMe CHF₂ Et CN 5-206 OMe CF₂Cl Et CN 5-207 OMe OMe Et CN 5-208 OMe NO₂ Et CN 5-209 OMe SO₂Me Et CN 5-210 SO₂Me Me Et CN 5-211 SO₂Me F Et CN 5-212 SO₂Me Cl Et CN 5-213 SO₂Me Br Et CN 5-214 SO₂Me I Et CN 5-215 SO₂Me CF₃ Et CN 5-216 SO₂Me CHF₂ Et CN 5-217 SO₂Me CF₂Cl Et CN 5-218 SO₂Me OMe Et CN 5-219 SO₂Me NO₂ Et CN 5-220 SO₂Me SO₂Me Et CN 5-221 Me Me CH₂CH₂OMe CN 5-222 Me F CH₂CH₂OMe CN 5-223 Me Cl CH₂CH₂OMe CN 5-224 Me Br CH₂CH₂OMe CN 5-225 Me I CH₂CH₂OMe CN 5-226 Me CF₃ CH₂CH₂OMe CN 5-227 Me CHF₂ CH₂CH₂OMe CN 5-228 Me CF₂Cl CH₂CH₂OMe CN 5-229 Me OMe CH₂CH₂OMe CN 5-230 Me NO₂ CH₂CH₂OMe CN 5-231 Me SO₂Me CH₂CH₂OMe CN 5-232 Cl Me CH₂CH₂OMe CN 5-233 Cl F CH₂CH₂OMe CN 5-234 Cl Cl CH₂CH₂OMe CN 5-235 Cl Br CH₂CH₂OMe CN 5-236 Cl I CH₂CH₂OMe CN 5-237 Cl CF₃ CH₂CH₂OMe CN 5-238 Cl CHF₂ CH₂CH₂OMe CN 5-239 Cl CF₂Cl CH₂CH₂OMe CN 5-240 Cl OMe CH₂CH₂OMe CN 5-241 Cl NO₂ CH₂CH₂OMe CN 5-242 Cl SO₂Me CH₂CH₂OMe CN 5-243 OMe Me CH₂CH₂OMe CN 5-244 OMe F CH₂CH₂OMe CN 5-245 OMe Cl CH₂CH₂OMe CN 5-246 OMe Br CH₂CH₂OMe CN 5-247 OMe I CH₂CH₂OMe CN 5-248 OMe CF₃ CH₂CH₂OMe CN 5-249 OMe CHF₂ CH₂CH₂OMe CN 5-250 OMe CF₂Cl CH₂CH₂OMe CN 5-251 OMe OMe CH₂CH₂OMe CN 5-252 OMe NO₂ CH₂CH₂OMe CN 5-253 OMe SO₂Me CH₂CH₂OMe CN 5-254 SO₂Me Me CH₂CH₂OMe CN 5-255 SO₂Me F CH₂CH₂OMe CN 5-256 SO₂Me Cl CH₂CH₂OMe CN 5-257 SO₂Me Br CH₂CH₂OMe CN 5-258 SO₂Me I CH₂CH₂OMe CN 5-259 SO₂Me CF₃ CH₂CH₂OMe CN 5-260 SO₂Me CHF₂ CH₂CH₂OMe CN 5-261 SO₂Me CF₂Cl CH₂CH₂OMe CN 5-262 SO₂Me OMe CH₂CH₂OMe CN 5-263 SO₂Me NO₂ CH₂CH₂OMe CN 5-264 SO₂Me SO₂Me CH₂CH₂OMe CN

TABLE 6 Compounds according to the invention of the formula (I) in which Q is Q5, W is hydrogen, t = 1 and the other radicals have the meanings indicated in the table

No. X Z R R′ Physical data (1H NMR) 6-1 Me Me Me H 6-2 Me F Me H 6-3 Me Cl Me H 6-4 Me Br Me H 6-5 Me I Me H 6-6 Me CF₃ Me H 6-7 Me CHF₂ Me H 6-8 Me CF₂Cl Me H 6-9 Me OMe Me H 6-10 Me NO₂ Me H 6-11 Me SO₂Me Me H 6-12 Cl Me Me H 6-13 Cl F Me H 6-14 Cl Cl Me H 6-15 Cl Br Me H 6-16 Cl I Me H 6-17 Cl CF₃ Me H 6-18 Cl CHF₂ Me H 6-19 Cl CF₂Cl Me H 6-20 Cl OMe Me H 6-21 Cl NO₂ Me H 6-22 Cl SO₂Me Me H 6-23 OMe Me Me H 6-24 OMe F Me H 6-25 OMe Cl Me H 6-26 OMe Br Me H 6-27 OMe I Me H 6-28 OMe CF₃ Me H 6-29 OMe CHF₂ Me H 6-30 OMe CF₂Cl Me H 6-31 OMe OMe Me H 6-32 OMe NO₂ Me H 6-33 OMe SO₂Me Me H 6-34 SO₂Me Me Me H 6-35 SO₂Me F Me H 6-36 SO₂Me Cl Me H 6-37 SO₂Me Br Me H 6-38 SO₂Me I Me H 6-39 SO₂Me CF₃ Me H 6-40 SO₂Me CHF₂ Me H 6-41 SO₂Me CF₂Cl Me H 6-42 SO₂Me OMe Me H 6-43 SO₂Me NO₂ Me H 6-44 SO₂Me SO₂Me Me H 6-45 Me Me Et H 6-46 Me F Et H 6-47 Me Cl Et H 6-48 Me Br Et H 6-49 Me I Et H 6-50 Me CF₃ Et H 6-51 Me CHF₂ Et H 6-52 Me CF₂Cl Et H 6-53 Me OMe Et H 6-54 Me NO₂ Et H 6-55 Me SO₂Me Et H 6-56 Cl Me Et H 6-57 Cl F Et H 6-58 Cl Cl Et H 6-59 Cl Br Et H 6-60 Cl I Et H 6-61 Cl CF₃ Et H 6-62 Cl CHF₂ Et H 6-63 Cl CF₂Cl Et H 6-64 Cl OMe Et H 6-65 Cl NO₂ Et H 6-66 Cl SO₂Me Et H 6-67 OMe Me Et H 6-68 OMe F Et H 6-69 OMe Cl Et H 6-70 OMe Br Et H 6-71 OMe I Et H 6-72 OMe CF₃ Et H 6-73 OMe CHF₂ Et H 6-74 OMe CF₂Cl Et H 6-75 OMe OMe Et H 6-76 OMe NO₂ Et H 6-77 OMe SO₂Me Et H 6-78 SO₂Me Me Et H 6-79 SO₂Me F Et H 6-80 SO₂Me Cl Et H 6-81 SO₂Me Br Et H 6-82 SO₂Me I Et H 6-83 SO₂Me CF₃ Et H 6-84 SO₂Me CHF₂ Et H 6-85 SO₂Me CF₂Cl Et H 6-86 SO₂Me OMe Et H 6-87 SO₂Me NO₂ Et H 6-88 SO₂Me SO₂Me Et H 6-89 Me Me CH₂CH₂OMe H 6-90 Me F CH₂CH₂OMe H 6-91 Me Cl CH₂CH₂OMe H 6-92 Me Br CH₂CH₂OMe H 6-93 Me I CH₂CH₂OMe H 6-94 Me CF₃ CH₂CH₂OMe H 6-95 Me CHF₂ CH₂CH₂OMe H 6-96 Me CF₂Cl CH₂CH₂OMe H 6-97 Me OMe CH₂CH₂OMe H 6-98 Me NO₂ CH₂CH₂OMe H 6-99 Me SO₂Me CH₂CH₂OMe H 6-100 Cl Me CH₂CH₂OMe H 6-101 Cl F CH₂CH₂OMe H 6-102 Cl Cl CH₂CH₂OMe H 6-103 Cl Br CH₂CH₂OMe H 6-104 Cl I CH₂CH₂OMe H 6-105 Cl CF₃ CH₂CH₂OMe H 6-106 Cl CHF₂ CH₂CH₂OMe H 6-107 Cl CF₂Cl CH₂CH₂OMe H 6-108 Cl OMe CH₂CH₂OMe H 6-109 Cl NO₂ CH₂CH₂OMe H 6-110 Cl SO₂Me CH₂CH₂OMe H 6-111 OMe Me CH₂CH₂OMe H 6-112 OMe F CH₂CH₂OMe H 6-113 OMe Cl CH₂CH₂OMe H 6-114 OMe Br CH₂CH₂OMe H 6-115 OMe I CH₂CH₂OMe H 6-116 OMe CF₃ CH₂CH₂OMe H 6-117 OMe CHF₂ CH₂CH₂OMe H 6-118 OMe CF₂Cl CH₂CH₂OMe H 6-119 OMe OMe CH₂CH₂OMe H 6-120 OMe NO₂ CH₂CH₂OMe H 6-121 OMe SO₂Me CH₂CH₂OMe H 6-122 SO₂Me Me CH₂CH₂OMe H 6-123 SO₂Me F CH₂CH₂OMe H 6-124 SO₂Me Cl CH₂CH₂OMe H 6-125 SO₂Me Br CH₂CH₂OMe H 6-126 SO₂Me I CH₂CH₂OMe H 6-127 SO₂Me CF₃ CH₂CH₂OMe H 6-128 SO₂Me CHF₂ CH₂CH₂OMe H 6-129 SO₂Me CF₂Cl CH₂CH₂OMe H 6-130 SO₂Me OMe CH₂CH₂OMe H 6-131 SO₂Me NO₂ CH₂CH₂OMe H 6-132 SO₂Me SO₂Me CH₂CH₂OMe H 6-133 Me Me Me CN 6-134 Me F Me CN 6-135 Me Cl Me CN 6-136 Me Br Me CN 6-137 Me I Me CN 6-138 Me CF₃ Me CN 6-139 Me CHF₂ Me CN 6-140 Me CF₂Cl Me CN 6-141 Me OMe Me CN 6-142 Me NO₂ Me CN 6-143 Me SO₂Me Me CN 6-144 Cl Me Me CN 6-145 Cl F Me CN 6-146 Cl Cl Me CN 6-147 Cl Br Me CN 6-148 Cl I Me CN 6-149 Cl CF₃ Me CN 6-150 Cl CHF₂ Me CN 6-151 Cl CF₂Cl Me CN 6-152 Cl OMe Me CN 6-153 Cl NO₂ Me CN 6-154 Cl SO₂Me Me CN 6-155 OMe Me Me CN 6-156 OMe F Me CN 6-157 OMe Cl Me CN 6-158 OMe Br Me CN 6-159 OMe I Me CN 6-160 OMe CF₃ Me CN 6-161 OMe CHF₂ Me CN 6-162 OMe CF₂Cl Me CN 6-163 OMe OMe Me CN 6-164 OMe NO₂ Me CN 6-165 OMe SO₂Me Me CN 6-166 SO₂Me Me Me CN 6-167 SO₂Me F Me CN 6-168 SO₂Me Cl Me CN 6-169 SO₂Me Br Me CN 6-170 SO₂Me I Me CN 6-171 SO₂Me CF₃ Me CN 6-172 SO₂Me CHF₂ Me CN 6-173 SO₂Me CF₂Cl Me CN 6-174 SO₂Me OMe Me CN 6-175 SO₂Me NO₂ Me CN 6-176 SO₂Me SO₂Me Me CN 6-177 Me Me Et CN 6-178 Me F Et CN 6-179 Me Cl Et CN 6-180 Me Br Et CN 6-181 Me I Et CN 6-182 Me CF₃ Et CN 6-183 Me CHF₂ Et CN 6-184 Me CF₂Cl Et CN 6-185 Me OMe Et CN 6-186 Me NO₂ Et CN 6-187 Me SO₂Me Et CN 6-188 Cl Me Et CN 6-189 Cl F Et CN 6-190 Cl Cl Et CN 6-191 Cl Br Et CN 6-192 Cl I Et CN 6-193 Cl CF₃ Et CN 6-194 Cl CHF₂ Et CN 6-195 Cl CF₂Cl Et CN 6-196 Cl OMe Et CN 6-197 Cl NO₂ Et CN 6-198 Cl SO₂Me Et CN 6-199 OMe Me Et CN 6-200 OMe F Et CN 6-201 OMe Cl Et CN 6-202 OMe Br Et CN 6-203 OMe I Et CN 6-204 OMe CF₃ Et CN 6-205 OMe CHF₂ Et CN 6-206 OMe CF₂Cl Et CN 6-207 OMe OMe Et CN 6-208 OMe NO₂ Et CN 6-209 OMe SO₂Me Et CN 6-210 SO₂Me Me Et CN 6-211 SO₂Me F Et CN 6-212 SO₂Me Cl Et CN 6-213 SO₂Me Br Et CN 6-214 SO₂Me I Et CN 6-215 SO₂Me CF₃ Et CN 6-216 SO₂Me CHF₂ Et CN 6-217 SO₂Me CF₂Cl Et CN 6-218 SO₂Me OMe Et CN 6-219 SO₂Me NO₂ Et CN 6-220 SO₂Me SO₂Me Et CN 6-221 Me Me CH₂CH₂OMe CN 6-222 Me F CH₂CH₂OMe CN 6-223 Me Cl CH₂CH₂OMe CN 6-224 Me Br CH₂CH₂OMe CN 6-225 Me I CH₂CH₂OMe CN 6-226 Me CF₃ CH₂CH₂OMe CN 6-227 Me CHF₂ CH₂CH₂OMe CN 6-228 Me CF₂Cl CH₂CH₂OMe CN 6-229 Me OMe CH₂CH₂OMe CN 6-230 Me NO₂ CH₂CH₂OMe CN 6-231 Me SO₂Me CH₂CH₂OMe CN 6-232 Cl Me CH₂CH₂OMe CN 6-233 Cl F CH₂CH₂OMe CN 6-234 Cl Cl CH₂CH₂OMe CN 6-235 Cl Br CH₂CH₂OMe CN 6-236 Cl I CH₂CH₂OMe CN 6-237 Cl CF₃ CH₂CH₂OMe CN 6-238 Cl CHF₂ CH₂CH₂OMe CN 6-239 Cl CF₂Cl CH₂CH₂OMe CN 6-240 Cl OMe CH₂CH₂OMe CN 6-241 Cl NO₂ CH₂CH₂OMe CN 6-242 Cl SO₂Me CH₂CH₂OMe CN 6-243 OMe Me CH₂CH₂OMe CN 6-244 OMe F CH₂CH₂OMe CN 6-245 OMe Cl CH₂CH₂OMe CN 6-246 OMe Br CH₂CH₂OMe CN 6-247 OMe I CH₂CH₂OMe CN 6-248 OMe CF₃ CH₂CH₂OMe CN 6-249 OMe CHF₂ CH₂CH₂OMe CN 6-250 OMe CF₂Cl CH₂CH₂OMe CN 6-251 OMe OMe CH₂CH₂OMe CN 6-252 OMe NO₂ CH₂CH₂OMe CN 6-253 OMe SO₂Me CH₂CH₂OMe CN 6-254 SO₂Me Me CH₂CH₂OMe CN 6-255 SO₂Me F CH₂CH₂OMe CN 6-256 SO₂Me Cl CH₂CH₂OMe CN 6-257 SO₂Me Br CH₂CH₂OMe CN 6-258 SO₂Me I CH₂CH₂OMe CN 6-259 SO₂Me CF₃ CH₂CH₂OMe CN 6-260 SO₂Me CHF₂ CH₂CH₂OMe CN 6-261 SO₂Me CF₂Cl CH₂CH₂OMe CN 6-262 SO₂Me OMe CH₂CH₂OMe CN 6-263 SO₂Me NO₂ CH₂CH₂OMe CN 6-264 SO₂Me SO₂Me CH₂CH₂OMe CN

TABLE 7 Compounds according to the invention of the formula (I) in the form of the sodium salts in which Q is Q3, R^(i) is methyl, R^(k) and W are each hydrogen, t = 1 and the other radicals have the meanings indicated in the table

No. X Z R R′ Physical data (1H NMR) 7-1 Me Me Me H 7-2 Me Cl Me H 7-3 Me CF₃ Me H 7-4 Me CHF₂ Me H 7-5 Cl Me Me H 7-6 Cl Cl Me H 7-7 Cl CF₃ Me H 7-8 Cl CHF₂ Me H 7-9 OMe Me Me H 7-10 OMe Cl Me H 7-11 OMe CF₃ Me H 7-12 OMe CHF₂ Me H 7-13 SO₂Me Me Me H 7-14 SO₂Me Cl Me H 7-15 SO₂Me CF₃ Me H 7-16 SO₂Me CHF₂ Me H 7-17 Me Me Et H 7-18 Me Cl Et H 7-19 Me CF₃ Et H 7-20 Me CHF₂ Et H 7-21 Cl Me Et H 7-22 Cl Cl Et H 7-23 Cl CF₃ Et H 7-24 Cl CHF₂ Et H 7-25 OMe Me Et H 7-26 OMe Cl Et H 7-27 OMe CF₃ Et H 7-28 OMe CHF₂ Et H 7-29 SO₂Me Me Et H 7-30 SO₂Me Cl Et H 7-31 SO₂Me CF₃ Et H 7-32 SO₂Me CHF₂ Et H 7-33 Me Me CH₂CH₂OMe H 7-34 Me Cl CH₂CH₂OMe H 7-35 Me CF₃ CH₂CH₂OMe H 7-36 Me CHF₂ CH₂CH₂OMe H 7-37 Cl Me CH₂CH₂OMe H 7-38 Cl Cl CH₂CH₂OMe H 7-39 Cl CF₃ CH₂CH₂OMe H 7-40 Cl CHF₂ CH₂CH₂OMe H 7-41 OMe Me CH₂CH₂OMe H 7-42 OMe Cl CH₂CH₂OMe H 7-43 OMe CF₃ CH₂CH₂OMe H 7-44 OMe CHF₂ CH₂CH₂OMe H 7-45 SO₂Me Me CH₂CH₂OMe H 7-46 SO₂Me Cl CH₂CH₂OMe H 7-47 SO₂Me CF₃ CH₂CH₂OMe H 7-48 SO₂Me CHF₂ CH₂CH₂OMe H 7-49 Me Me Me CN 7-50 Me Cl Me CN 7-51 Me CF₃ Me CN 7-52 Me CHF₂ Me CN 7-53 Cl Me Me CN 7-54 Cl Cl Me CN 7-55 Cl CF₃ Me CN 7-56 Cl CHF₂ Me CN 7-57 OMe Me Me CN 7-58 OMe Cl Me CN 7-59 OMe CF₃ Me CN 7-60 OMe CHF₂ Me CN 7-61 SO₂Me Me Me CN 7-62 SO₂Me Cl Me CN 7-63 SO₂Me CF₃ Me CN 7-64 SO₂Me CHF₂ Me CN 7-65 Me Me Et CN 7-66 Me Cl Et CN 7-67 Me CF₃ Et CN 7-68 Me CHF₂ Et CN 7-69 Cl Me Et CN 7-70 Cl Cl Et CN 7-71 Cl CF₃ Et CN 7-72 Cl CHF₂ Et CN 7-73 OMe Me Et CN 7-74 OMe Cl Et CN 7-75 OMe CF₃ Et CN 7-76 OMe CHF₂ Et CN 7-77 SO₂Me Me Et CN 7-78 SO₂Me Cl Et CN 7-79 SO₂Me CF₃ Et CN 7-80 SO₂Me CHF₂ Et CN 7-81 Me Me CH₂CH₂OMe CN 7-82 Me Cl CH₂CH₂OMe CN 7-83 Me CF₃ CH₂CH₂OMe CN 7-84 Me CHF₂ CH₂CH₂OMe CN 7-85 Cl Me CH₂CH₂OMe CN 7-86 Cl Cl CH₂CH₂OMe CN 7-87 Cl CF₃ CH₂CH₂OMe CN 7-88 Cl CHF₂ CH₂CH₂OMe CN 7-89 OMe Me CH₂CH₂OMe CN 7-90 OMe Cl CH₂CH₂OMe CN 7-91 OMe CF₃ CH₂CH₂OMe CN 7-92 OMe CHF₂ CH₂CH₂OMe CN 7-93 SO₂Me Me CH₂CH₂OMe CN 7-94 SO₂Me Cl CH₂CH₂OMe CN 7-95 SO₂Me CF₃ CH₂CH₂OMe CN 7-96 SO₂Me CHF₂ CH₂CH₂OMe CN

TABLE 8 Compounds according to the invention of the formula (I) in which Q is Q1, R^(a) is a hydroxyl group, the radicals R^(b), R^(c), R^(d), R^(e), R^(f), R^(g) and W are each hydrogen, t = 0 and the other radicals have the meanings indicated in the table

No. X Z R R′ Physical data (¹H NMR) 8-1 Me Me Me H 8-2 Me F Me H 8-3 Me Cl Me H 8-4 Me Br Me H 8-5 Me I Me H 8-6 Me CF₃ Me H 8-7 Me CHF₂ Me H 8-8 Me CF₂Cl Me H 8-9 Me OMe Me H 8-10 Me NO₂ Me H 8-11 Me SO₂Me Me H 8-12 Cl Me Me H 8-13 Cl F Me H 8-14 Cl Cl Me H 8-15 Cl Br Me H 8-16 Cl I Me H 8-17 Cl CF₃ Me H 8-18 Cl CHF₂ Me H 8-19 Cl CF₂Cl Me H 8-20 Cl OMe Me H 8-21 Cl NO₂ Me H 8-22 Cl SO₂Me Me H 8-23 OMe Me Me H 8-24 OMe F Me H 8-25 OMe Cl Me H 8-26 OMe Br Me H 8-27 OMe I Me H 8-28 OMe CF₃ Me H 8-29 OMe CHF₂ Me H 8-30 OMe CF₂Cl Me H 8-31 OMe OMe Me H 8-32 OMe NO₂ Me H 8-33 OMe SO₂Me Me H 8-34 SO₂Me Me Me H 8-35 SO₂Me F Me H 8-36 SO₂Me Cl Me H 8-37 SO₂Me Br Me H 8-38 SO₂Me I Me H 8-39 SO₂Me CF₃ Me H 8-40 SO₂Me CHF₂ Me H 8-41 SO₂Me CF₂Cl Me H 8-42 SO₂Me OMe Me H 8-43 SO₂Me NO₂ Me H 8-44 SO₂Me SO₂Me Me H 8-45 Me Me Et H 8-46 Me F Et H 8-47 Me Cl Et H 8-48 Me Br Et H 8-49 Me I Et H 8-50 Me CF₃ Et H 8-51 Me CHF₂ Et H 8-52 Me CF₂Cl Et H 8-53 Me OMe Et H 8-54 Me NO₂ Et H 8-55 Me SO₂Me Et H 8-56 Cl Me Et H 8-57 Cl F Et H 8-58 Cl Cl Et H 8-59 Cl Br Et H 8-60 Cl I Et H 8-61 Cl CF₃ Et H 8-62 Cl CHF₂ Et H 8-63 Cl CF₂Cl Et H 8-64 Cl OMe Et H 8-65 Cl NO₂ Et H 8-66 Cl SO₂Me Et H 8-67 OMe Me Et H 8-68 OMe F Et H 8-69 OMe Cl Et H 8-70 OMe Br Et H 8-71 OMe I Et H 8-72 OMe CF₃ Et H 8-73 OMe CHF₂ Et H 8-74 OMe CF₂Cl Et H 8-75 OMe OMe Et H 8-76 OMe NO₂ Et H 8-77 OMe SO₂Me Et H 8-78 SO₂Me Me Et H 8-79 SO₂Me F Et H 8-80 SO₂Me Cl Et H 8-81 SO₂Me Br Et H 8-82 SO₂Me I Et H 8-83 SO₂Me CF₃ Et H 8-84 SO₂Me CHF₂ Et H 8-85 SO₂Me CF₂Cl Et H 8-86 SO₂Me OMe Et H 8-87 SO₂Me NO₂ Et H 8-88 SO₂Me SO₂Me Et H 8-89 Me Me CH₂CH₂OMe H 8-90 Me F CH₂CH₂OMe H 8-91 Me Cl CH₂CH₂OMe H 8-92 Me Br CH₂CH₂OMe H 8-93 Me I CH₂CH₂OMe H 8-94 Me CF₃ CH₂CH₂OMe H 8-95 Me CHF₂ CH₂CH₂OMe H 8-96 Me CF₂Cl CH₂CH₂OMe H 8-97 Me OMe CH₂CH₂OMe H 8-98 Me NO₂ CH₂CH₂OMe H 8-99 Me SO₂Me CH₂CH₂OMe H 8-100 Cl Me CH₂CH₂OMe H 8-101 Cl F CH₂CH₂OMe H 8-102 Cl Cl CH₂CH₂OMe H 8-103 Cl Br CH₂CH₂OMe H 8-104 Cl I CH₂CH₂OMe H 8-105 Cl CF₃ CH₂CH₂OMe H 8-106 Cl CHF₂ CH₂CH₂OMe H 8-107 Cl CF₂Cl CH₂CH₂OMe H 8-108 Cl OMe CH₂CH₂OMe H 8-109 Cl NO₂ CH₂CH₂OMe H 8-110 Cl SO₂Me CH₂CH₂OMe H 8-111 OMe Me CH₂CH₂OMe H 8-112 OMe F CH₂CH₂OMe H 8-113 OMe Cl CH₂CH₂OMe H 8-114 OMe Br CH₂CH₂OMe H 8-115 OMe I CH₂CH₂OMe H 8-116 OMe CF₃ CH₂CH₂OMe H 8-117 OMe CHF₂ CH₂CH₂OMe H 8-118 OMe CF₂Cl CH₂CH₂OMe H 8-119 OMe OMe CH₂CH₂OMe H 8-120 OMe NO₂ CH₂CH₂OMe H 8-121 OMe SO₂Me CH₂CH₂OMe H 8-122 SO₂Me Me CH₂CH₂OMe H 8-123 SO₂Me F CH₂CH₂OMe H 8-124 SO₂Me Cl CH₂CH₂OMe H 8-125 SO₂Me Br CH₂CH₂OMe H 8-126 SO₂Me I CH₂CH₂OMe H 8-127 SO₂Me CF₃ CH₂CH₂OMe H 8-128 SO₂Me CHF₂ CH₂CH₂OMe H 8-129 SO₂Me CF₂Cl CH₂CH₂OMe H 8-130 SO₂Me OMe CH₂CH₂OMe H 8-131 SO₂Me NO₂ CH₂CH₂OMe H 8-132 SO₂Me SO₂Me CH₂CH₂OMe H 8-133 Me Me Me CN 8-134 Me F Me CN 8-135 Me Cl Me CN 8-136 Me Br Me CN 8-137 Me I Me CN 8-138 Me CF₃ Me CN 8-139 Me CHF₂ Me CN 8-140 Me CF₂Cl Me CN 8-141 Me OMe Me CN 8-142 Me NO₂ Me CN 8-143 Me SO₂Me Me CN 8-144 Cl Me Me CN 8-145 Cl F Me CN 8-146 Cl Cl Me CN 8-147 Cl Br Me CN 8-148 Cl I Me CN 8-149 Cl CF₃ Me CN 8-150 Cl CHF₂ Me CN 8-151 Cl CF₂Cl Me CN 8-152 Cl OMe Me CN 8-153 Cl NO₂ Me CN 8-154 Cl SO₂Me Me CN 8-155 OMe Me Me CN 8-156 OMe F Me CN 8-157 OMe Cl Me CN 8-158 OMe Br Me CN 8-159 OMe I Me CN 8-160 OMe CF₃ Me CN 8-161 OMe CHF₂ Me CN 8-162 OMe CF₂Cl Me CN 8-163 OMe OMe Me CN 8-164 OMe NO₂ Me CN 8-165 OMe SO₂Me Me CN 8-166 SO₂Me Me Me CN 8-167 SO₂Me F Me CN 8-168 SO₂Me Cl Me CN 8-169 SO₂Me Br Me CN 8-170 SO₂Me I Me CN 8-171 SO₂Me CF₃ Me CN 8-172 SO₂Me CHF₂ Me CN 8-173 SO₂Me CF₂Cl Me CN 8-174 SO₂Me OMe Me CN 8-175 SO₂Me NO₂ Me CN 8-176 SO₂Me SO₂Me Me CN 8-177 Me Me Et CN 8-178 Me F Et CN 8-179 Me Cl Et CN 8-180 Me Br Et CN 8-181 Me I Et CN 8-182 Me CF₃ Et CN 8-183 Me CHF₂ Et CN 8-184 Me CF₂Cl Et CN 8-185 Me OMe Et CN 8-186 Me NO₂ Et CN 8-187 Me SO₂Me Et CN 8-188 Cl Me Et CN 8-189 Cl F Et CN 8-190 Cl Cl Et CN 8-191 Cl Br Et CN 8-192 Cl I Et CN 8-193 Cl CF₃ Et CN 8-194 Cl CHF₂ Et CN 8-195 Cl CF₂Cl Et CN 8-196 Cl OMe Et CN 8-197 Cl NO₂ Et CN 8-198 Cl SO₂Me Et CN 8-199 OMe Me Et CN 8-200 OMe F Et CN 8-201 OMe Cl Et CN 8-202 OMe Br Et CN 8-203 OMe I Et CN 8-204 OMe CF₃ Et CN 8-205 OMe CHF₂ Et CN 8-206 OMe CF₂Cl Et CN 8-207 OMe OMe Et CN 8-208 OMe NO₂ Et CN 8-209 OMe SO₂Me Et CN 8-210 SO₂Me Me Et CN 8-211 SO₂Me F Et CN 8-212 SO₂Me Cl Et CN 8-213 SO₂Me Br Et CN 8-214 SO₂Me I Et CN 8-215 SO₂Me CF₃ Et CN 8-216 SO₂Me CHF₂ Et CN 8-217 SO₂Me CF₂Cl Et CN 8-218 SO₂Me OMe Et CN 8-219 SO₂Me NO₂ Et CN 8-220 SO₂Me SO₂Me Et CN 8-221 Me Me CH₂CH₂OMe CN 8-222 Me F CH₂CH₂OMe CN 8-223 Me Cl CH₂CH₂OMe CN 8-224 Me Br CH₂CH₂OMe CN 8-225 Me I CH₂CH₂OMe CN 8-226 Me CF₃ CH₂CH₂OMe CN 8-227 Me CHF₂ CH₂CH₂OMe CN 8-228 Me CF₂Cl CH₂CH₂OMe CN 8-229 Me OMe CH₂CH₂OMe CN 8-230 Me NO₂ CH₂CH₂OMe CN 8-231 Me SO₂Me CH₂CH₂OMe CN 8-232 Cl Me CH₂CH₂OMe CN 8-233 Cl F CH₂CH₂OMe CN 8-234 Cl Cl CH₂CH₂OMe CN 8-235 Cl Br CH₂CH₂OMe CN 8-236 Cl I CH₂CH₂OMe CN 8-237 Cl CF₃ CH₂CH₂OMe CN 8-238 Cl CHF₂ CH₂CH₂OMe CN 8-239 Cl CF₂Cl CH₂CH₂OMe CN 8-240 Cl OMe CH₂CH₂OMe CN 8-241 Cl NO₂ CH₂CH₂OMe CN 8-242 Cl SO₂Me CH₂CH₂OMe CN 8-243 OMe Me CH₂CH₂OMe CN 8-244 OMe F CH₂CH₂OMe CN 8-245 OMe Cl CH₂CH₂OMe CN 8-246 OMe Br CH₂CH₂OMe CN 8-247 OMe I CH₂CH₂OMe CN 8-248 OMe CF₃ CH₂CH₂OMe CN 8-249 OMe CHF₂ CH₂CH₂OMe CN 8-250 OMe CF₂Cl CH₂CH₂OMe CN 8-251 OMe OMe CH₂CH₂OMe CN 8-252 OMe NO₂ CH₂CH₂OMe CN 8-253 OMe SO₂Me CH₂CH₂OMe CN 8-254 SO₂Me Me CH₂CH₂OMe CN 8-255 SO₂Me F CH₂CH₂OMe CN 8-256 SO₂Me Cl CH₂CH₂OMe CN 8-257 SO₂Me Br CH₂CH₂OMe CN 8-258 SO₂Me I CH₂CH₂OMe CN 8-259 SO₂Me CF₃ CH₂CH₂OMe CN 8-260 SO₂Me CHF₂ CH₂CH₂OMe CN 8-261 SO₂Me CF₂Cl CH₂CH₂OMe CN 8-262 SO₂Me OMe CH₂CH₂OMe CN 8-263 SO₂Me NO₂ CH₂CH₂OMe CN 8-264 SO₂Me SO₂Me CH₂CH₂OMe CN

TABLE 9 Compounds according to the invention of the formula (I) in which Q is Q2, R^(a) is a hydroxyl group, R^(b), R^(f) and W are each hydrogen, A is CH₂CH₂, Y is CH₂, t = 0 and the other radicals have the meanings indicated in the table

Physical data No. X Z R R′ (¹H NMR) 9-1 Me Me Me H 9-2 Me F Me H 9-3 Me Cl Me H 9-4 Me Br Me H 9-5 Me I Me H 9-6 Me CF₃ Me H 9-7 Me CHF₂ Me H 9-8 Me CF₂Cl Me H 9-9 Me OMe Me H 9-10 Me NO₂ Me H 9-11 Me SO₂Me Me H 9-12 Cl Me Me H 9-13 Cl F Me H 9-14 Cl Cl Me H 9-15 Cl Br Me H 9-16 Cl I Me H 9-17 Cl CF₃ Me H 9-18 Cl CHF₂ Me H 9-19 Cl CF₂Cl Me H 9-20 Cl OMe Me H 9-21 Cl NO₂ Me H 9-22 Cl SO₂Me Me H 9-23 OMe Me Me H 9-24 OMe F Me H 9-25 OMe Cl Me H 9-26 OMe Br Me H 9-27 OMe I Me H 9-28 OMe CF₃ Me H 9-29 OMe CHF₂ Me H 9-30 OMe CF₂Cl Me H 9-31 OMe OMe Me H 9-32 OMe NO₂ Me H 9-33 OMe SO₂Me Me H 9-34 SO₂Me Me Me H 9-35 SO₂Me F Me H 9-36 SO₂Me Cl Me H 9-37 SO₂Me Br Me H 9-38 SO₂Me I Me H 9-39 SO₂Me CF₃ Me H 9-40 SO₂Me CHF₂ Me H 9-41 SO₂Me CF₂Cl Me H 9-42 SO₂Me OMe Me H 9-43 SO₂Me NO₂ Me H 9-44 SO₂Me SO₂Me Me H 9-45 Me Me Et H 9-46 Me F Et H 9-47 Me Cl Et H 9-48 Me Br Et H 9-49 Me I Et H 9-50 Me CF₃ Et H 9-51 Me CHF₂ Et H 9-52 Me CF₂Cl Et H 9-53 Me OMe Et H 9-54 Me NO₂ Et H 9-55 Me SO₂Me Et H 9-56 Cl Me Et H 9-57 Cl F Et H 9-58 Cl Cl Et H 9-59 Cl Br Et H 9-60 Cl I Et H 9-61 Cl CF₃ Et H 9-62 Cl CHF₂ Et H 9-63 Cl CF₂Cl Et H 9-64 Cl OMe Et H 9-65 Cl NO₂ Et H 9-66 Cl SO₂Me Et H 9-67 OMe Me Et H 9-68 OMe F Et H 9-69 OMe Cl Et H 9-70 OMe Br Et H 9-71 OMe I Et H 9-72 OMe CF₃ Et H 9-73 OMe CHF₂ Et H 9-74 OMe CF₂Cl Et H 9-75 OMe OMe Et H 9-76 OMe NO₂ Et H 9-77 OMe SO₂Me Et H 9-78 SO₂Me Me Et H 9-79 SO₂Me F Et H 9-80 SO₂Me Cl Et H 9-81 SO₂Me Br Et H 9-82 SO₂Me I Et H 9-83 SO₂Me CF₃ Et H 9-84 SO₂Me CHF₂ Et H 9-85 SO₂Me CF₂Cl Et H 9-86 SO₂Me OMe Et H 9-87 SO₂Me NO₂ Et H 9-88 SO₂Me SO₂Me Et H 9-89 Me Me CH₂CH₂OMe H 9-90 Me F CH₂CH₂OMe H 9-91 Me Cl CH₂CH₂OMe H 9-92 Me Br CH₂CH₂OMe H 9-93 Me I CH₂CH₂OMe H 9-94 Me CF₃ CH₂CH₂OMe H 9-95 Me CHF₂ CH₂CH₂OMe H 9-96 Me CF₂Cl CH₂CH₂OMe H 9-97 Me OMe CH₂CH₂OMe H 9-98 Me NO₂ CH₂CH₂OMe H 9-99 Me SO₂Me CH₂CH₂OMe H 9-100 Cl Me CH₂CH₂OMe H 9-101 Cl F CH₂CH₂OMe H 9-102 Cl Cl CH₂CH₂OMe H 9-103 Cl Br CH₂CH₂OMe H 9-104 Cl I CH₂CH₂OMe H 9-105 Cl CF₃ CH₂CH₂OMe H 9-106 Cl CHF₂ CH₂CH₂OMe H 9-107 Cl CF₂Cl CH₂CH₂OMe H 9-108 Cl OMe CH₂CH₂OMe H 9-109 Cl NO₂ CH₂CH₂OMe H 9-110 Cl SO₂Me CH₂CH₂OMe H 9-111 OMe Me CH₂CH₂OMe H 9-112 OMe F CH₂CH₂OMe H 9-113 OMe Cl CH₂CH₂OMe H 9-114 OMe Br CH₂CH₂OMe H 9-115 OMe I CH₂CH₂OMe H 9-116 OMe CF₃ CH₂CH₂OMe H 9-117 OMe CHF₂ CH₂CH₂OMe H 9-118 OMe CF₂Cl CH₂CH₂OMe H 9-119 OMe OMe CH₂CH₂OMe H 9-120 OMe NO₂ CH₂CH₂OMe H 9-121 OMe SO₂Me CH₂CH₂OMe H 9-122 SO₂Me Me CH₂CH₂OMe H 9-123 SO₂Me F CH₂CH₂OMe H 9-124 SO₂Me Cl CH₂CH₂OMe H 9-125 SO₂Me Br CH₂CH₂OMe H 9-126 SO₂Me I CH₂CH₂OMe H 9-127 SO₂Me CF₃ CH₂CH₂OMe H 9-128 SO₂Me CHF₂ CH₂CH₂OMe H 9-129 SO₂Me CF₂Cl CH₂CH₂OMe H 9-130 SO₂Me OMe CH₂CH₂OMe H 9-131 SO₂Me NO₂ CH₂CH₂OMe H 9-132 SO₂Me SO₂Me CH₂CH₂OMe H 9-133 Me Me Me CN 9-134 Me F Me CN 9-135 Me Cl Me CN 9-136 Me Br Me CN 9-137 Me I Me CN 9-138 Me CF₃ Me CN 9-139 Me CHF₂ Me CN 9-140 Me CF₂Cl Me CN 9-141 Me OMe Me CN 9-142 Me NO₂ Me CN 9-143 Me SO₂Me Me CN 9-144 Cl Me Me CN 9-145 Cl F Me CN 9-146 Cl Cl Me CN 9-147 Cl Br Me CN 9-148 Cl I Me CN 9-149 Cl CF₃ Me CN 9-150 Cl CHF₂ Me CN 9-151 Cl CF₂Cl Me CN 9-152 Cl OMe Me CN 9-153 Cl NO₂ Me CN 9-154 Cl SO₂Me Me CN 9-155 OMe Me Me CN 9-156 OMe F Me CN 9-157 OMe Cl Me CN 9-158 OMe Br Me CN 9-159 OMe I Me CN 9-160 OMe CF₃ Me CN 9-161 OMe CHF₂ Me CN 9-162 OMe CF₂Cl Me CN 9-163 OMe OMe Me CN 9-164 OMe NO₂ Me CN 9-165 OMe SO₂Me Me CN 9-166 SO₂Me Me Me CN 9-167 SO₂Me F Me CN 9-168 SO₂Me Cl Me CN 9-169 SO₂Me Br Me CN 9-170 SO₂Me I Me CN 9-171 SO₂Me CF₃ Me CN 9-172 SO₂Me CHF₂ Me CN 9-173 SO₂Me CF₂Cl Me CN 9-174 SO₂Me OMe Me CN 9-175 SO₂Me NO₂ Me CN 9-176 SO₂Me SO₂Me Me CN 9-177 Me Me Et CN 9-178 Me F Et CN 9-179 Me Cl Et CN 9-180 Me Br Et CN 9-181 Me I Et CN 9-182 Me CF₃ Et CN 9-183 Me CHF₂ Et CN 9-184 Me CF₂Cl Et CN 9-185 Me OMe Et CN 9-186 Me NO₂ Et CN 9-187 Me SO₂Me Et CN 9-188 Cl Me Et CN 9-189 Cl F Et CN 9-190 Cl Cl Et CN 9-191 Cl Br Et CN 9-192 Cl I Et CN 9-193 Cl CF₃ Et CN 9-194 Cl CHF₂ Et CN 9-195 Cl CF₂Cl Et CN 9-196 Cl OMe Et CN 9-197 Cl NO₂ Et CN 9-198 Cl SO₂Me Et CN 9-199 OMe Me Et CN 9-200 OMe F Et CN 9-201 OMe Cl Et CN 9-202 OMe Br Et CN 9-203 OMe I Et CN 9-204 OMe CF₃ Et CN 9-205 OMe CHF₂ Et CN 9-206 OMe CF₂Cl Et CN 9-207 OMe OMe Et CN 9-208 OMe NO₂ Et CN 9-209 OMe SO₂Me Et CN 9-210 SO₂Me Me Et CN 9-211 SO₂Me F Et CN 9-212 SO₂Me Cl Et CN 9-213 SO₂Me Br Et CN 9-214 SO₂Me I Et CN 9-215 SO₂Me CF₃ Et CN 9-216 SO₂Me CHF₂ Et CN 9-217 SO₂Me CF₂Cl Et CN 9-218 SO₂Me OMe Et CN 9-219 SO₂Me NO₂ Et CN 9-220 SO₂Me SO₂Me Et CN 9-221 Me Me CH₂CH₂OMe CN 9-222 Me F CH₂CH₂OMe CN 9-223 Me Cl CH₂CH₂OMe CN 9-224 Me Br CH₂CH₂OMe CN 9-225 Me I CH₂CH₂OMe CN 9-226 Me CF₃ CH₂CH₂OMe CN 9-227 Me CHF₂ CH₂CH₂OMe CN 9-228 Me CF₂Cl CH₂CH₂OMe CN 9-229 Me OMe CH₂CH₂OMe CN 9-230 Me NO₂ CH₂CH₂OMe CN 9-231 Me SO₂Me CH₂CH₂OMe CN 9-232 Cl Me CH₂CH₂OMe CN 9-233 Cl F CH₂CH₂OMe CN 9-234 Cl Cl CH₂CH₂OMe CN 9-235 Cl Br CH₂CH₂OMe CN 9-236 Cl I CH₂CH₂OMe CN 9-237 Cl CF₃ CH₂CH₂OMe CN 9-238 Cl CHF₂ CH₂CH₂OMe CN 9-239 Cl CF₂Cl CH₂CH₂OMe CN 9-240 Cl OMe CH₂CH₂OMe CN 9-241 Cl NO₂ CH₂CH₂OMe CN 9-242 Cl SO₂Me CH₂CH₂OMe CN 9-243 OMe Me CH₂CH₂OMe CN 9-244 OMe F CH₂CH₂OMe CN 9-245 OMe Cl CH₂CH₂OMe CN 9-246 OMe Br CH₂CH₂OMe CN 9-247 OMe I CH₂CH₂OMe CN 9-248 OMe CF₃ CH₂CH₂OMe CN 9-249 OMe CHF₂ CH₂CH₂OMe CN 9-250 OMe CF₂Cl CH₂CH₂OMe CN 9-251 OMe OMe CH₂CH₂OMe CN 9-252 OMe NO₂ CH₂CH₂OMe CN 9-253 OMe SO₂Me CH₂CH₂OMe CN 9-254 SO₂Me Me CH₂CH₂OMe CN 9-255 SO₂Me F CH₂CH₂OMe CN 9-256 SO₂Me Cl CH₂CH₂OMe CN 9-257 SO₂Me Br CH₂CH₂OMe CN 9-258 SO₂Me I CH₂CH₂OMe CN 9-259 SO₂Me CF₃ CH₂CH₂OMe CN 9-260 SO₂Me CHF₂ CH₂CH₂OMe CN 9-261 SO₂Me CF₂Cl CH₂CH₂OMe CN 9-262 SO₂Me OMe CH₂CH₂OMe CN 9-263 SO₂Me NO₂ CH₂CH₂OMe CN 9-264 SO₂Me SO₂Me CH₂CH₂OMe CN

TABLE 10 Compounds according to the invention of the formula (I) in which Q is Q3, R^(i) is methyl and R^(h), R^(k) and W are each hydrogen, t = 0 and the other radicals have the meanings indicated in the table

Physical data No. X Z R R′ (¹H NMR) 10-1 Me Me Me H 10-2 Me F Me H 10-3 Me Cl Me H 10-4 Me Br Me H 10-5 Me I Me H 10-6 Me CF₃ Me H 10-7 Me CHF₂ Me H 10-8 Me CF₂Cl Me H 10-9 Me OMe Me H 10-10 Me NO₂ Me H 10-11 Me SO₂Me Me H 10-12 Cl Me Me H 10-13 Cl F Me H 10-14 Cl Cl Me H 10-15 Cl Br Me H 10-16 Cl I Me H 10-17 Cl CF₃ Me H 10-18 Cl CHF₂ Me H 10-19 Cl CF₂Cl Me H 10-20 Cl OMe Me H 10-21 Cl NO₂ Me H 10-22 Cl SO₂Me Me H 10-23 OMe Me Me H 10-24 OMe F Me H 10-25 OMe Cl Me H 10-26 OMe Br Me H 10-27 OMe I Me H 10-28 OMe CF₃ Me H 10-29 OMe CHF₂ Me H 10-30 OMe CF₂Cl Me H 10-31 OMe OMe Me H 10-32 OMe NO₂ Me H 10-33 OMe SO₂Me Me H 10-34 SO₂Me Me Me H 10-35 SO₂Me F Me H 10-36 SO₂Me Cl Me H 10-37 SO₂Me Br Me H 10-38 SO₂Me I Me H 10-39 SO₂Me CF₃ Me H 10-40 SO₂Me CHF₂ Me H 10-41 SO₂Me CF₂Cl Me H 10-42 SO₂Me OMe Me H 10-43 SO₂Me NO₂ Me H 10-44 SO₂Me SO₂Me Me H 10-45 Me Me Et H 10-46 Me F Et H 10-47 Me Cl Et H 10-48 Me Br Et H 10-49 Me I Et H 10-50 Me CF₃ Et H 10-51 Me CHF₂ Et H 10-52 Me CF₂Cl Et H 10-53 Me OMe Et H 10-54 Me NO₂ Et H 10-55 Me SO₂Me Et H 10-56 Cl Me Et H 10-57 Cl F Et H 10-58 Cl Cl Et H 10-59 Cl Br Et H 10-60 Cl I Et H 10-61 Cl CF₃ Et H 10-62 Cl CHF₂ Et H 10-63 Cl CF₂Cl Et H 10-64 Cl OMe Et H 10-65 Cl NO₂ Et H 10-66 Cl SO₂Me Et H 10-67 OMe Me Et H 10-68 OMe F Et H 10-69 OMe Cl Et H 10-70 OMe Br Et H 10-71 OMe I Et H 10-72 OMe CF₃ Et H 10-73 OMe CHF₂ Et H 10-74 OMe CF₂Cl Et H 10-75 OMe OMe Et H 10-76 OMe NO₂ Et H 10-77 OMe SO₂Me Et H 10-78 SO₂Me Me Et H 10-79 SO₂Me F Et H 10-80 SO₂Me Cl Et H 10-81 SO₂Me Br Et H 10-82 SO₂Me I Et H 10-83 SO₂Me CF₃ Et H 10-84 SO₂Me CHF₂ Et H 10-85 SO₂Me CF₂Cl Et H 10-86 SO₂Me OMe Et H 10-87 SO₂Me NO₂ Et H 10-88 SO₂Me SO₂Me Et H 10-89 Me Me CH₂CH₂OMe H 10-90 Me F CH₂CH₂OMe H 10-91 Me Cl CH₂CH₂OMe H 10-92 Me Br CH₂CH₂OMe H 10-93 Me I CH₂CH₂OMe H 10-94 Me CF₃ CH₂CH₂OMe H 10-95 Me CHF₂ CH₂CH₂OMe H 10-96 Me CF₂Cl CH₂CH₂OMe H 10-97 Me OMe CH₂CH₂OMe H 10-98 Me NO₂ CH₂CH₂OMe H 10-99 Me SO₂Me CH₂CH₂OMe H 10-100 Cl Me CH₂CH₂OMe H 10-101 Cl F CH₂CH₂OMe H 10-102 Cl Cl CH₂CH₂OMe H 10-103 Cl Br CH₂CH₂OMe H 10-104 Cl I CH₂CH₂OMe H 10-105 Cl CF₃ CH₂CH₂OMe H 10-106 Cl CHF₂ CH₂CH₂OMe H 10-107 Cl CF₂Cl CH₂CH₂OMe H 10-108 Cl OMe CH₂CH₂OMe H 10-109 Cl NO₂ CH₂CH₂OMe H 10-110 Cl SO₂Me CH₂CH₂OMe H 10-111 OMe Me CH₂CH₂OMe H 10-112 OMe F CH₂CH₂OMe H 10-113 OMe Cl CH₂CH₂OMe H 10-114 OMe Br CH₂CH₂OMe H 10-115 OMe I CH₂CH₂OMe H 10-116 OMe CF₃ CH₂CH₂OMe H 10-117 OMe CHF₂ CH₂CH₂OMe H 10-118 OMe CF₂Cl CH₂CH₂OMe H 10-119 OMe OMe CH₂CH₂OMe H 10-120 OMe NO₂ CH₂CH₂OMe H 10-121 OMe SO₂Me CH₂CH₂OMe H 10-122 SO₂Me Me CH₂CH₂OMe H 10-123 SO₂Me F CH₂CH₂OMe H 10-124 SO₂Me Cl CH₂CH₂OMe H 10-125 SO₂Me Br CH₂CH₂OMe H 10-126 SO₂Me I CH₂CH₂OMe H 10-127 SO₂Me CF₃ CH₂CH₂OMe H 10-128 SO₂Me CHF₂ CH₂CH₂OMe H 10-129 SO₂Me CF₂Cl CH₂CH₂OMe H 10-130 SO₂Me OMe CH₂CH₂OMe H 10-131 SO₂Me NO₂ CH₂CH₂OMe H 10-132 SO₂Me SO₂Me CH₂CH₂OMe H 10-133 Me Me Me CN 10-134 Me F Me CN 10-135 Me Cl Me CN 10-136 Me Br Me CN 10-137 Me I Me CN 10-138 Me CF₃ Me CN 10-139 Me CHF₂ Me CN 10-140 Me CF₂Cl Me CN 10-141 Me OMe Me CN 10-142 Me NO₂ Me CN 10-143 Me SO₂Me Me CN 10-144 Cl Me Me CN 10-145 Cl F Me CN 10-146 Cl Cl Me CN 10-147 Cl Br Me CN 10-148 Cl I Me CN 10-149 Cl CF₃ Me CN 10-150 Cl CHF₂ Me CN 10-151 Cl CF₂Cl Me CN 10-152 Cl OMe Me CN 10-153 Cl NO₂ Me CN 10-154 Cl SO₂Me Me CN 10-155 OMe Me Me CN 10-156 OMe F Me CN 10-157 OMe Cl Me CN 10-158 OMe Br Me CN 10-159 OMe I Me CN 10-160 OMe CF₃ Me CN 10-161 OMe CHF₂ Me CN 10-162 OMe CF₂Cl Me CN 10-163 OMe OMe Me CN 10-164 OMe NO₂ Me CN 10-165 OMe SO₂Me Me CN 10-166 SO₂Me Me Me CN 10-167 SO₂Me F Me CN 10-168 SO₂Me Cl Me CN 10-169 SO₂Me Br Me CN 10-170 SO₂Me I Me CN 10-171 SO₂Me CF₃ Me CN 10-172 SO₂Me CHF₂ Me CN 10-173 SO₂Me CF₂Cl Me CN 10-174 SO₂Me OMe Me CN 10-175 SO₂Me NO₂ Me CN 10-176 SO₂Me SO₂Me Me CN 10-177 Me Me Et CN 10-178 Me F Et CN 10-179 Me Cl Et CN 10-180 Me Br Et CN 10-181 Me I Et CN 10-182 Me CF₃ Et CN 10-183 Me CHF₂ Et CN 10-184 Me CF₂Cl Et CN 10-185 Me OMe Et CN 10-186 Me NO₂ Et CN 10-187 Me SO₂Me Et CN 10-188 Cl Me Et CN 10-189 Cl F Et CN 10-190 Cl Cl Et CN 10-191 Cl Br Et CN 10-192 Cl I Et CN 10-193 Cl CF₃ Et CN 10-194 Cl CHF₂ Et CN 10-195 Cl CF₂Cl Et CN 10-196 Cl OMe Et CN 10-197 Cl NO₂ Et CN 10-198 Cl SO₂Me Et CN 10-199 OMe Me Et CN 10-200 OMe F Et CN 10-201 OMe Cl Et CN 10-202 OMe Br Et CN 10-203 OMe I Et CN 10-204 OMe CF₃ Et CN 10-205 OMe CHF₂ Et CN 10-206 OMe CF₂Cl Et CN 10-207 OMe OMe Et CN 10-208 OMe NO₂ Et CN 10-209 OMe SO₂Me Et CN 10-210 SO₂Me Me Et CN 10-211 SO₂Me F Et CN 10-212 SO₂Me Cl Et CN 10-213 SO₂Me Br Et CN 10-214 SO₂Me I Et CN 10-215 SO₂Me CF₃ Et CN 10-216 SO₂Me CHF₂ Et CN 10-217 SO₂Me CF₂Cl Et CN 10-218 SO₂Me OMe Et CN 10-219 SO₂Me NO₂ Et CN 10-220 SO₂Me SO₂Me Et CN 10-221 Me Me CH₂CH₂OMe CN 10-222 Me F CH₂CH₂OMe CN 10-223 Me Cl CH₂CH₂OMe CN 10-224 Me Br CH₂CH₂OMe CN 10-225 Me I CH₂CH₂OMe CN 10-226 Me CF₃ CH₂CH₂OMe CN 10-227 Me CHF₂ CH₂CH₂OMe CN 10-228 Me CF₂Cl CH₂CH₂OMe CN 10-229 Me OMe CH₂CH₂OMe CN 10-230 Me NO₂ CH₂CH₂OMe CN 10-231 Me SO₂Me CH₂CH₂OMe CN 10-232 Cl Me CH₂CH₂OMe CN 10-233 Cl F CH₂CH₂OMe CN 10-234 Cl Cl CH₂CH₂OMe CN 10-235 Cl Br CH₂CH₂OMe CN 10-236 Cl I CH₂CH₂OMe CN 10-237 Cl CF₃ CH₂CH₂OMe CN 10-238 Cl CHF₂ CH₂CH₂OMe CN 10-239 Cl CF₂Cl CH₂CH₂OMe CN 10-240 Cl OMe CH₂CH₂OMe CN 10-241 Cl NO₂ CH₂CH₂OMe CN 10-242 Cl SO₂Me CH₂CH₂OMe CN 10-243 OMe Me CH₂CH₂OMe CN 10-244 OMe F CH₂CH₂OMe CN 10-245 OMe Cl CH₂CH₂OMe CN 10-246 OMe Br CH₂CH₂OMe CN 10-247 OMe I CH₂CH₂OMe CN 10-248 OMe CF₃ CH₂CH₂OMe CN 10-249 OMe CHF₂ CH₂CH₂OMe CN 10-250 OMe CF₂Cl CH₂CH₂OMe CN 10-251 OMe OMe CH₂CH₂OMe CN 10-252 OMe NO₂ CH₂CH₂OMe CN 10-253 OMe SO₂Me CH₂CH₂OMe CN 10-254 SO₂Me Me CH₂CH₂OMe CN 10-255 SO₂Me F CH₂CH₂OMe CN 10-256 SO₂Me Cl CH₂CH₂OMe CN 10-257 SO₂Me Br CH₂CH₂OMe CN 10-258 SO₂Me I CH₂CH₂OMe CN 10-259 SO₂Me CF₃ CH₂CH₂OMe CN 10-260 SO₂Me CHF₂ CH₂CH₂OMe CN 10-261 SO₂Me CF₂Cl CH₂CH₂OMe CN 10-262 SO₂Me OMe CH₂CH₂OMe CN 10-263 SO₂Me NO₂ CH₂CH₂OMe CN 10-264 SO₂Me SO₂Me CH₂CH₂OMe CN

TABLE 10a Compounds according to the invention of the formula (I) in which Q is Q3, R^(i) is ethyl and R^(h), R^(k) and W are each hydrogen, t = 0 and the other radicals have the meanings indicated in the table

No. X Z R R′ Physical data (¹H NMR) 10a-1 Me Me Me H 10a-2 Me F Me H 10a-3 Me Cl Me H 10a-4 Me Br Me H 10a-5 Me I Me H 10a-6 Me CF₃ Me H 10a-7 Me CHF₂ Me H 10a-8 Me CF₂Cl Me H 10a-9 Me OMe Me H 10a-10 Me NO₂ Me H 10a-11 Me SO₂Me Me H 10a-12 Cl Me Me H 10a-13 Cl F Me H 10a-14 Cl Cl Me H 10a-15 Cl Br Me H 10a-16 Cl I Me H 10a-17 Cl CF₃ Me H 10a-18 Cl CHF₂ Me H 10a-19 Cl CF₂Cl Me H 10a-20 Cl OMe Me H 10a-21 Cl NO₂ Me H 10a-22 Cl SO₂Me Me H 10a-23 OMe Me Me H 10a-24 OMe F Me H 10a-25 OMe Cl Me H 10a-26 OMe Br Me H 10a-27 OMe I Me H 10a-28 OMe CF₃ Me H 10a-29 OMe CHF₂ Me H 10a-30 OMe CF₂Cl Me H 10a-31 OMe OMe Me H 10a-32 OMe NO₂ Me H 10a-33 OMe SO₂Me Me H 10a-34 SO₂Me Me Me H 10a-35 SO₂Me F Me H 10a-36 SO₂Me Cl Me H 10a-37 SO₂Me Br Me H 10a-38 SO₂Me I Me H 10a-39 SO₂Me CF₃ Me H 10a-40 SO₂Me CHF₂ Me H 10a-41 SO₂Me CF₂Cl Me H 10a-42 SO₂Me OMe Me H 10a-43 SO₂Me NO₂ Me H 10a-44 SO₂Me SO₂Me Me H 10a-45 Me Me Et H 10a-46 Me F Et H 10a-47 Me Cl Et H 10a-48 Me Br Et H 10a-49 Me I Et H 10a-50 Me CF₃ Et H 10a-51 Me CHF₂ Et H 10a-52 Me CF₂Cl Et H 10a-53 Me OMe Et H 10a-54 Me NO₂ Et H 10a-55 Me SO₂Me Et H 10a-56 Cl Me Et H 10a-57 Cl F Et H 10a-58 Cl Cl Et H 10a-59 Cl Br Et H 10a-60 Cl I Et H 10a-61 Cl CF₃ Et H 10a-62 Cl CHF₂ Et H 10a-63 Cl CF₂Cl Et H 10a-64 Cl OMe Et H 10a-65 Cl NO₂ Et H 10a-66 Cl SO₂Me Et H 10a-67 OMe Me Et H 10a-68 OMe F Et H 10a-69 OMe Cl Et H 10a-70 OMe Br Et H 10a-71 OMe I Et H 10a-72 OMe CF₃ Et H 10a-73 OMe CHF₂ Et H 10a-74 OMe CF₂Cl Et H 10a-75 OMe OMe Et H 10a-76 OMe NO₂ Et H 10a-77 OMe SO₂Me Et H 10a-78 SO₂Me Me Et H 10a-79 SO₂Me F Et H 10a-80 SO₂Me Cl Et H 10a-81 SO₂Me Br Et H 10a-82 SO₂Me I Et H 10a-83 SO₂Me CF₃ Et H 10a-84 SO₂Me CHF₂ Et H 10a-85 SO₂Me CF₂Cl Et H 10a-86 SO₂Me OMe Et H 10a-87 SO₂Me NO₂ Et H 10a-88 SO₂Me SO₂Me Et H 10a-89 Me Me CH₂CH₂OMe H 10a-90 Me F CH₂CH₂OMe H 10a-91 Me Cl CH₂CH₂OMe H 10a-92 Me Br CH₂CH₂OMe H 10a-93 Me I CH₂CH₂OMe H 10a-94 Me CF₃ CH₂CH₂OMe H 10a-95 Me CHF₂ CH₂CH₂OMe H 10a-96 Me CF₂Cl CH₂CH₂OMe H 10a-97 Me OMe CH₂CH₂OMe H 10a-98 Me NO₂ CH₂CH₂OMe H 10a-99 Me SO₂Me CH₂CH₂OMe H 10a-100 Cl Me CH₂CH₂OMe H 10a-101 Cl F CH₂CH₂OMe H 10a-102 Cl Cl CH₂CH₂OMe H 10a-103 Cl Br CH₂CH₂OMe H 10a-104 Cl I CH₂CH₂OMe H 10a-105 Cl CF₃ CH₂CH₂OMe H 10a-106 Cl CHF₂ CH₂CH₂OMe H 10a-107 Cl CF₂Cl CH₂CH₂OMe H 10a-108 Cl OMe CH₂CH₂OMe H 10a-109 Cl NO₂ CH₂CH₂OMe H 10a-110 Cl SO₂Me CH₂CH₂OMe H 10a-111 OMe Me CH₂CH₂OMe H 10a-112 OMe F CH₂CH₂OMe H 10a-113 OMe Cl CH₂CH₂OMe H 10a-114 OMe Br CH₂CH₂OMe H 10a-115 OMe I CH₂CH₂OMe H 10a-116 OMe CF₃ CH₂CH₂OMe H 10a-117 OMe CHF₂ CH₂CH₂OMe H 10a-118 OMe CF₂Cl CH₂CH₂OMe H 10a-119 OMe OMe CH₂CH₂OMe H 10a-120 OMe NO₂ CH₂CH₂OMe H 10a-121 OMe SO₂Me CH₂CH₂OMe H 10a-122 SO₂Me Me CH₂CH₂OMe H 10a-123 SO₂Me F CH₂CH₂OMe H 10a-124 SO₂Me Cl CH₂CH₂OMe H 10a-125 SO₂Me Br CH₂CH₂OMe H 10a-126 SO₂Me I CH₂CH₂OMe H 10a-127 SO₂Me CF₃ CH₂CH₂OMe H 10a-128 SO₂Me CHF₂ CH₂CH₂OMe H 10a-129 SO₂Me CF₂Cl CH₂CH₂OMe H 10a-130 SO₂Me OMe CH₂CH₂OMe H 10a-131 SO₂Me NO₂ CH₂CH₂OMe H 10a-132 SO₂Me SO₂Me CH₂CH₂OMe H 10a-133 Me Me Me CN 10a-134 Me F Me CN 10a-135 Me Cl Me CN 10a-136 Me Br Me CN 10a-137 Me I Me CN 10a-138 Me CF₃ Me CN 10a-139 Me CHF₂ Me CN 10a-140 Me CF₂Cl Me CN 10a-141 Me OMe Me CN 10a-142 Me NO₂ Me CN 10a-143 Me SO₂Me Me CN 10a-144 Cl Me Me CN 10a-145 Cl F Me CN 10a-146 Cl Cl Me CN 10a-147 Cl Br Me CN 10a-148 Cl I Me CN 10a-149 Cl CF₃ Me CN 10a-150 Cl CHF₂ Me CN 10a-151 Cl CF₂Cl Me CN 10a-152 Cl OMe Me CN 10a-153 Cl NO₂ Me CN 10a-154 Cl SO₂Me Me CN 10a-155 OMe Me Me CN 10a-156 OMe F Me CN 10a-157 OMe Cl Me CN 10a-158 OMe Br Me CN 10a-159 OMe I Me CN 10a-160 OMe CF₃ Me CN (400 MHz, CDCl₃ δ, ppm) 7.82 (d, 1H), 7.61 (d, 1H), 7.48 (s, 1H), 4.12 (q, 2H), 4.06 (s, 3H), 3.36 (s, 3H), 1.48 (t, 3H) 10a-161 OMe CHF₂ Me CN 10a-162 OMe CF₂Cl Me CN 10a-163 OMe OMe Me CN 10a-164 OMe NO₂ Me CN 10a-165 OMe SO₂Me Me CN 10a-166 SO₂Me Me Me CN 10a-167 SO₂Me F Me CN 10a-168 SO₂Me Cl Me CN 10a-169 SO₂Me Br Me CN 10a-170 SO₂Me I Me CN 10a-171 SO₂Me CF₃ Me CN 10a-172 SO₂Me CHF₂ Me CN 10a-173 SO₂Me CF₂Cl Me CN 10a-174 SO₂Me OMe Me CN 10a-175 SO₂Me NO₂ Me CN 10a-176 SO₂Me SO₂Me Me CN 10a-177 Me Me Et CN 10a-178 Me F Et CN 10a-179 Me Cl Et CN 10a-180 Me Br Et CN 10a-181 Me I Et CN 10a-182 Me CF₃ Et CN 10a-183 Me CHF₂ Et CN 10a-184 Me CF₂Cl Et CN 10a-185 Me OMe Et CN 10a-186 Me NO₂ Et CN 10a-187 Me SO₂Me Et CN 10a-188 Cl Me Et CN 10a-189 Cl F Et CN 10a-190 Cl Cl Et CN 10a-191 Cl Br Et CN 10a-192 Cl I Et CN 10a-193 Cl CF₃ Et CN 10a-194 Cl CHF₂ Et CN 10a-195 Cl CF₂Cl Et CN 10a-196 Cl OMe Et CN 10a-197 Cl NO₂ Et CN 10a-198 Cl SO₂Me Et CN 10a-199 OMe Me Et CN 10a-200 OMe F Et CN 10a-201 OMe Cl Et CN 10a-202 OMe Br Et CN 10a-203 OMe I Et CN 10a-204 OMe CF₃ Et CN 10a-205 OMe CHF₂ Et CN 10a-206 OMe CF₂Cl Et CN 10a-207 OMe OMe Et CN 10a-208 OMe NO₂ Et CN 10a-209 OMe SO₂Me Et CN 10a-210 SO₂Me Me Et CN 10a-211 SO₂Me F Et CN 10a-212 SO₂Me Cl Et CN 10a-213 SO₂Me Br Et CN 10a-214 SO₂Me I Et CN 10a-215 SO₂Me CF₃ Et CN 10a-216 SO₂Me CHF₂ Et CN 10a-217 SO₂Me CF₂Cl Et CN 10a-218 SO₂Me OMe Et CN 10a-219 SO₂Me NO₂ Et CN 10a-220 SO₂Me SO₂Me Et CN 10a-221 Me Me CH₂CH₂OMe CN 10a-222 Me F CH₂CH₂OMe CN 10a-223 Me Cl CH₂CH₂OMe CN 10a-224 Me Br CH₂CH₂OMe CN 10a-225 Me I CH₂CH₂OMe CN 10a-226 Me CF₃ CH₂CH₂OMe CN 10a-227 Me CHF₂ CH₂CH₂OMe CN 10a-228 Me CF₂Cl CH₂CH₂OMe CN 10a-229 Me OMe CH₂CH₂OMe CN 10a-230 Me NO₂ CH₂CH₂OMe CN 10a-231 Me SO₂Me CH₂CH₂OMe CN 10a-232 Cl Me CH₂CH₂OMe CN 10a-233 Cl F CH₂CH₂OMe CN 10a-234 Cl Cl CH₂CH₂OMe CN 10a-235 Cl Br CH₂CH₂OMe CN 10a-236 Cl I CH₂CH₂OMe CN 10a-237 Cl CF₃ CH₂CH₂OMe CN 10a-238 Cl CHF₂ CH₂CH₂OMe CN 10a-239 Cl CF₂Cl CH₂CH₂OMe CN 10a-240 Cl OMe CH₂CH₂OMe CN 10a-241 Cl NO₂ CH₂CH₂OMe CN 10a-242 Cl SO₂Me CH₂CH₂OMe CN 10a-243 OMe Me CH₂CH₂OMe CN 10a-244 OMe F CH₂CH₂OMe CN 10a-245 OMe Cl CH₂CH₂OMe CN 10a-246 OMe Br CH₂CH₂OMe CN 10a-247 OMe I CH₂CH₂OMe CN 10a-248 OMe CF₃ CH₂CH₂OMe CN 10a-249 OMe CHF₂ CH₂CH₂OMe CN 10a-250 OMe CF₂Cl CH₂CH₂OMe CN 10a-251 OMe OMe CH₂CH₂OMe CN 10a-252 OMe NO₂ CH₂CH₂OMe CN 10a-253 OMe SO₂Me CH₂CH₂OMe CN 10a-254 SO₂Me Me CH₂CH₂OMe CN 10a-255 SO₂Me F CH₂CH₂OMe CN 10a-256 SO₂Me Cl CH₂CH₂OMe CN 10a-257 SO₂Me Br CH₂CH₂OMe CN 10a-258 SO₂Me I CH₂CH₂OMe CN 10a-259 SO₂Me CF₃ CH₂CH₂OMe CN 10a-260 SO₂Me CHF₂ CH₂CH₂OMe CN 10a-261 SO₂Me CF₂Cl CH₂CH₂OMe CN 10a-262 SO₂Me OMe CH₂CH₂OMe CN 10a-263 SO₂Me NO₂ CH₂CH₂OMe CN 10a-264 SO₂Me SO₂Me CH₂CH₂OMe CN

TABLE 11 Compounds according to the invention of the formula (I) in which Q is Q3, R^(i) and R^(k) is in each case methyl, R^(h) and W are each hydrogen, t = 0 and the other radicals have the meanings indicated in the table

Physical data No. X Z R R′ (1H NMR) 11-1 Me Me Me H 11-2 Me F Me H 11-3 Me Cl Me H 11-4 Me Br Me H 11-5 Me I Me H 11-6 Me CF₃ Me H 11-7 Me CHF₂ Me H 11-8 Me CF₂Cl Me H 11-9 Me OMe Me H 11-10 Me NO₂ Me H 11-11 Me SO₂Me Me H 11-12 Cl Me Me H 11-13 Cl F Me H 11-14 Cl Cl Me H 11-15 Cl Br Me H 11-16 Cl I Me H 11-17 Cl CF₃ Me H 11-18 Cl CHF₂ Me H 11-19 Cl CF₂Cl Me H 11-20 Cl OMe Me H 11-21 Cl NO₂ Me H 11-22 Cl SO₂Me Me H 11-23 OMe Me Me H 11-24 OMe F Me H 11-25 OMe Cl Me H 11-26 OMe Br Me H 11-27 OMe I Me H 11-28 OMe CF₃ Me H 11-29 OMe CHF₂ Me H 11-30 OMe CF₂Cl Me H 11-31 OMe OMe Me H 11-32 OMe NO₂ Me H 11-33 OMe SO₂Me Me H 11-34 SO₂Me Me Me H 11-35 SO₂Me F Me H 11-36 SO₂Me Cl Me H 11-37 SO₂Me Br Me H 11-38 SO₂Me I Me H 11-39 SO₂Me CF₃ Me H 11-40 SO₂Me CHF₂ Me H 11-41 SO₂Me CF₂Cl Me H 11-42 SO₂Me OMe Me H 11-43 SO₂Me NO₂ Me H 11-44 SO₂Me SO₂Me Me H 11-45 Me Me Et H 11-46 Me F Et H 11-47 Me Cl Et H 11-48 Me Br Et H 11-49 Me I Et H 11-50 Me CF₃ Et H 11-51 Me CHF₂ Et H 11-52 Me CF₂Cl Et H 11-53 Me OMe Et H 11-54 Me NO₂ Et H 11-55 Me SO₂Me Et H 11-56 Cl Me Et H 11-57 Cl F Et H 11-58 Cl Cl Et H 11-59 Cl Br Et H 11-60 Cl I Et H 11-61 Cl CF₃ Et H 11-62 Cl CHF₂ Et H 11-63 Cl CF₂Cl Et H 11-64 Cl OMe Et H 11-65 Cl NO₂ Et H 11-66 Cl SO₂Me Et H 11-67 OMe Me Et H 11-68 OMe F Et H 11-69 OMe Cl Et H 11-70 OMe Br Et H 11-71 OMe I Et H 11-72 OMe CF₃ Et H 11-73 OMe CHF₂ Et H 11-74 OMe CF₂Cl Et H 11-75 OMe OMe Et H 11-76 OMe NO₂ Et H 11-77 OMe SO₂Me Et H 11-78 SO₂Me Me Et H 11-79 SO₂Me F Et H 11-80 SO₂Me Cl Et H 11-81 SO₂Me Br Et H 11-82 SO₂Me I Et H 11-83 SO₂Me CF₃ Et H 11-84 SO₂Me CHF₂ Et H 11-85 SO₂Me CF₂Cl Et H 11-86 SO₂Me OMe Et H 11-87 SO₂Me NO₂ Et H 11-88 SO₂Me SO₂Me Et H 11-89 Me Me CH₂CH₂OMe H 11-90 Me F CH₂CH₂OMe H 11-91 Me Cl CH₂CH₂OMe H 11-92 Me Br CH₂CH₂OMe H 11-93 Me I CH₂CH₂OMe H 11-94 Me CF₃ CH₂CH₂OMe H 11-95 Me CHF₂ CH₂CH₂OMe H 11-96 Me CF₂Cl CH₂CH₂OMe H 11-97 Me OMe CH₂CH₂OMe H 11-98 Me NO₂ CH₂CH₂OMe H 11-99 Me SO₂Me CH₂CH₂OMe H 11-100 Cl Me CH₂CH₂OMe H 11-101 Cl F CH₂CH₂OMe H 11-102 Cl Cl CH₂CH₂OMe H 11-103 Cl Br CH₂CH₂OMe H 11-104 Cl I CH₂CH₂OMe H 11-105 Cl CF₃ CH₂CH₂OMe H 11-106 Cl CHF₂ CH₂CH₂OMe H 11-107 Cl CF₂Cl CH₂CH₂OMe H 11-108 Cl OMe CH₂CH₂OMe H 11-109 Cl NO₂ CH₂CH₂OMe H 11-110 Cl SO₂Me CH₂CH₂OMe H 11-111 OMe Me CH₂CH₂OMe H 11-112 OMe F CH₂CH₂OMe H 11-113 OMe Cl CH₂CH₂OMe H 11-114 OMe Br CH₂CH₂OMe H 11-115 OMe I CH₂CH₂OMe H 11-116 OMe CF₃ CH₂CH₂OMe H 11-117 OMe CHF₂ CH₂CH₂OMe H 11-118 OMe CF₂Cl CH₂CH₂OMe H 11-119 OMe OMe CH₂CH₂OMe H 11-120 OMe NO₂ CH₂CH₂OMe H 11-121 OMe SO₂Me CH₂CH₂OMe H 11-122 SO₂Me Me CH₂CH₂OMe H 11-123 SO₂Me F CH₂CH₂OMe H 11-124 SO₂Me Cl CH₂CH₂OMe H 11-125 SO₂Me Br CH₂CH₂OMe H 11-126 SO₂Me I CH₂CH₂OMe H 11-127 SO₂Me CF₃ CH₂CH₂OMe H 11-128 SO₂Me CHF₂ CH₂CH₂OMe H 11-129 SO₂Me CF₂Cl CH₂CH₂OMe H 11-130 SO₂Me OMe CH₂CH₂OMe H 11-131 SO₂Me NO₂ CH₂CH₂OMe H 11-132 SO₂Me SO₂Me CH₂CH₂OMe H 11-133 Me Me Me CN 11-134 Me F Me CN 11-135 Me Cl Me CN 11-136 Me Br Me CN 11-137 Me I Me CN 11-138 Me CF₃ Me CN 11-139 Me CHF₂ Me CN 11-140 Me CF₂Cl Me CN 11-141 Me OMe Me CN 11-142 Me NO₂ Me CN 11-143 Me SO₂Me Me CN 11-144 Cl Me Me CN 11-145 Cl F Me CN 11-146 Cl Cl Me CN 11-147 Cl Br Me CN 11-148 Cl I Me CN 11-149 Cl CF₃ Me CN 11-150 Cl CHF₂ Me CN 11-151 Cl CF₂Cl Me CN 11-152 Cl OMe Me CN 11-153 Cl NO₂ Me CN 11-154 Cl SO₂Me Me CN 11-155 OMe Me Me CN 11-156 OMe F Me CN 11-157 OMe Cl Me CN 11-158 OMe Br Me CN 11-159 OMe I Me CN 11-160 OMe CF₃ Me CN 11-161 OMe CHF₂ Me CN 11-162 OMe CF₂Cl Me CN 11-163 OMe OMe Me CN 11-164 OMe NO₂ Me CN 11-165 OMe SO₂Me Me CN 11-166 SO₂Me Me Me CN 11-167 SO₂Me F Me CN 11-168 SO₂Me Cl Me CN 11-169 SO₂Me Br Me CN 11-170 SO₂Me I Me CN 11-171 SO₂Me CF₃ Me CN 11-172 SO₂Me CHF₂ Me CN 11-173 SO₂Me CF₂Cl Me CN 11-174 SO₂Me OMe Me CN 11-175 SO₂Me NO₂ Me CN 11-176 SO₂Me SO₂Me Me CN 11-177 Me Me Et CN 11-178 Me F Et CN 11-179 Me Cl Et CN 11-180 Me Br Et CN 11-181 Me I Et CN 11-182 Me CF₃ Et CN 11-183 Me CHF₂ Et CN 11-184 Me CF₂Cl Et CN 11-185 Me OMe Et CN 11-186 Me NO₂ Et CN 11-187 Me SO₂Me Et CN 11-188 Cl Me Et CN 11-189 Cl F Et CN 11-190 Cl Cl Et CN 11-191 Cl Br Et CN 11-192 Cl I Et CN 11-193 Cl CF₃ Et CN 11-194 Cl CHF₂ Et CN 11-195 Cl CF₂Cl Et CN 11-196 Cl OMe Et CN 11-197 Cl NO₂ Et CN 11-198 Cl SO₂Me Et CN 11-199 OMe Me Et CN 11-200 OMe F Et CN 11-201 OMe Cl Et CN 11-202 OMe Br Et CN 11-203 OMe I Et CN 11-204 OMe CF₃ Et CN 11-205 OMe CHF₂ Et CN 11-206 OMe CF₂Cl Et CN 11-207 OMe OMe Et CN 11-208 OMe NO₂ Et CN 11-209 OMe SO₂Me Et CN 11-210 SO₂Me Me Et CN 11-211 SO₂Me F Et CN 11-212 SO₂Me Cl Et CN 11-213 SO₂Me Br Et CN 11-214 SO₂Me I Et CN 11-215 SO₂Me CF₃ Et CN 11-216 SO₂Me CHF₂ Et CN 11-217 SO₂Me CF₂Cl Et CN 11-218 SO₂Me OMe Et CN 11-219 SO₂Me NO₂ Et CN 11-220 SO₂Me SO₂Me Et CN 11-221 Me Me CH₂CH₂OMe CN 11-222 Me F CH₂CH₂OMe CN 11-223 Me Cl CH₂CH₂OMe CN 11-224 Me Br CH₂CH₂OMe CN 11-225 Me I CH₂CH₂OMe CN 11-226 Me CF₃ CH₂CH₂OMe CN 11-227 Me CHF₂ CH₂CH₂OMe CN 11-228 Me CF₂Cl CH₂CH₂OMe CN 11-229 Me OMe CH₂CH₂OMe CN 11-230 Me NO₂ CH₂CH₂OMe CN 11-231 Me SO₂Me CH₂CH₂OMe CN 11-232 Cl Me CH₂CH₂OMe CN 11-233 Cl F CH₂CH₂OMe CN 11-234 Cl Cl CH₂CH₂OMe CN 11-235 Cl Br CH₂CH₂OMe CN 11-236 Cl I CH₂CH₂OMe CN 11-237 Cl CF₃ CH₂CH₂OMe CN 11-238 Cl CHF₂ CH₂CH₂OMe CN 11-239 Cl CF₂Cl CH₂CH₂OMe CN 11-240 Cl OMe CH₂CH₂OMe CN 11-241 Cl NO₂ CH₂CH₂OMe CN 11-242 Cl SO₂Me CH₂CH₂OMe CN 11-243 OMe Me CH₂CH₂OMe CN 11-244 OMe F CH₂CH₂OMe CN 11-245 OMe Cl CH₂CH₂OMe CN 11-246 OMe Br CH₂CH₂OMe CN 11-247 OMe I CH₂CH₂OMe CN 11-248 OMe CF₃ CH₂CH₂OMe CN 11-249 OMe CHF₂ CH₂CH₂OMe CN 11-250 OMe CF₂Cl CH₂CH₂OMe CN 11-251 OMe OMe CH₂CH₂OMe CN 11-252 OMe NO₂ CH₂CH₂OMe CN 11-253 OMe SO₂Me CH₂CH₂OMe CN 11-254 SO₂Me Me CH₂CH₂OMe CN 11-255 SO₂Me F CH₂CH₂OMe CN 11-256 SO₂Me Cl CH₂CH₂OMe CN 11-257 SO₂Me Br CH₂CH₂OMe CN 11-258 SO₂Me I CH₂CH₂OMe CN 11-259 SO₂Me CF₃ CH₂CH₂OMe CN 11-260 SO₂Me CHF₂ CH₂CH₂OMe CN 11-261 SO₂Me CF₂Cl CH₂CH₂OMe CN 11-262 SO₂Me OMe CH₂CH₂OMe CN 11-263 SO₂Me NO₂ CH₂CH₂OMe CN 11-264 SO₂Me SO₂Me CH₂CH₂OMe CN

TABLE 12 Compounds according to the invention of the formula (I) in which Q is Q4, W is hydrogen, t = 0 and the other radicals have the meanings indicated in the table

No. X Z R R′ Physical data (1H NMR) 12-1 Me Me Me H 12-2 Me F Me H 12-3 Me Cl Me H 12-4 Me Br Me H 12-5 Me I Me H 12-6 Me CF₃ Me H 12-7 Me CHF₂ Me H 12-8 Me CF₂Cl Me H 12-9 Me OMe Me H 12-10 Me NO₂ Me H 12-11 Me SO₂Me Me H 12-12 Cl Me Me H 12-13 Cl F Me H 12-14 Cl Cl Me H 12-15 Cl Br Me H 12-16 Cl I Me H 12-17 Cl CF₃ Me H 12-18 Cl CHF₂ Me H 12-19 Cl CF₂Cl Me H 12-20 Cl OMe Me H 12-21 Cl NO₂ Me H 12-22 Cl SO₂Me Me H 12-23 OMe Me Me H 12-24 OMe F Me H 12-25 OMe Cl Me H 12-26 OMe Br Me H 12-27 OMe I Me H 12-28 OMe CF₃ Me H 12-29 OMe CHF₂ Me H 12-30 OMe CF₂Cl Me H 12-31 OMe OMe Me H 12-32 OMe NO₂ Me H 12-33 OMe SO₂Me Me H 12-34 SO₂Me Me Me H 12-35 SO₂Me F Me H 12-36 SO₂Me Cl Me H 12-37 SO₂Me Br Me H 12-38 SO₂Me I Me H 12-39 SO₂Me CF₃ Me H 12-40 SO₂Me CHF₂ Me H 12-41 SO₂Me CF₂Cl Me H 12-42 SO₂Me OMe Me H 12-43 SO₂Me NO₂ Me H 12-44 SO₂Me SO₂Me Me H 12-45 Me Me Et H 12-46 Me F Et H 12-47 Me Cl Et H 12-48 Me Br Et H 12-49 Me I Et H 12-50 Me CF₃ Et H 12-51 Me CHF₂ Et H 12-52 Me CF₂Cl Et H 12-53 Me OMe Et H 12-54 Me NO₂ Et H 12-55 Me SO₂Me Et H 12-56 Cl Me Et H 12-57 Cl F Et H 12-58 Cl Cl Et H 12-59 Cl Br Et H 12-60 Cl I Et H 12-61 Cl CF₃ Et H 12-62 Cl CHF₂ Et H 12-63 Cl CF₂Cl Et H 12-64 Cl OMe Et H 12-65 Cl NO₂ Et H 12-66 Cl SO₂Me Et H 12-67 OMe Me Et H 12-68 OMe F Et H 12-69 OMe Cl Et H 12-70 OMe Br Et H 12-71 OMe I Et H 12-72 OMe CF₃ Et H 12-73 OMe CHF₂ Et H 12-74 OMe CF₂Cl Et H 12-75 OMe OMe Et H 12-76 OMe NO₂ Et H 12-77 OMe SO₂Me Et H 12-78 SO₂Me Me Et H 12-79 SO₂Me F Et H 12-80 SO₂Me Cl Et H 12-81 SO₂Me Br Et H 12-82 SO₂Me I Et H 12-83 SO₂Me CF₃ Et H 12-84 SO₂Me CHF₂ Et H 12-85 SO₂Me CF₂Cl Et H 12-86 SO₂Me OMe Et H 12-87 SO₂Me NO₂ Et H 12-88 SO₂Me SO₂Me Et H 12-89 Me Me CH₂CH₂OMe H 12-90 Me F CH₂CH₂OMe H 12-91 Me Cl CH₂CH₂OMe H 12-92 Me Br CH₂CH₂OMe H 12-93 Me I CH₂CH₂OMe H 12-94 Me CF₃ CH₂CH₂OMe H 12-95 Me CHF₂ CH₂CH₂OMe H 12-96 Me CF₂Cl CH₂CH₂OMe H 12-97 Me OMe CH₂CH₂OMe H 12-98 Me NO₂ CH₂CH₂OMe H 12-99 Me SO₂Me CH₂CH₂OMe H 12-100 Cl Me CH₂CH₂OMe H 12-101 Cl F CH₂CH₂OMe H 12-102 Cl Cl CH₂CH₂OMe H 12-103 Cl Br CH₂CH₂OMe H 12-104 Cl I CH₂CH₂OMe H 12-105 Cl CF₃ CH₂CH₂OMe H 12-106 Cl CHF₂ CH₂CH₂OMe H 12-107 Cl CF₂Cl CH₂CH₂OMe H 12-108 Cl OMe CH₂CH₂OMe H 12-109 Cl NO₂ CH₂CH₂OMe H 12-110 Cl SO₂Me CH₂CH₂OMe H 12-111 OMe Me CH₂CH₂OMe H 12-112 OMe F CH₂CH₂OMe H 12-113 OMe Cl CH₂CH₂OMe H 12-114 OMe Br CH₂CH₂OMe H 12-115 OMe I CH₂CH₂OMe H 12-116 OMe CF₃ CH₂CH₂OMe H 12-117 OMe CHF₂ CH₂CH₂OMe H 12-118 OMe CF₂Cl CH₂CH₂OMe H 12-119 OMe OMe CH₂CH₂OMe H 12-120 OMe NO₂ CH₂CH₂OMe H 12-121 OMe SO₂Me CH₂CH₂OMe H 12-122 SO₂Me Me CH₂CH₂OMe H 12-123 SO₂Me F CH₂CH₂OMe H 12-124 SO₂Me Cl CH₂CH₂OMe H 12-125 SO₂Me Br CH₂CH₂OMe H 12-126 SO₂Me I CH₂CH₂OMe H 12-127 SO₂Me CF₃ CH₂CH₂OMe H 12-128 SO₂Me CHF₂ CH₂CH₂OMe H 12-129 SO₂Me CF₂Cl CH₂CH₂OMe H 12-130 SO₂Me OMe CH₂CH₂OMe H 12-131 SO₂Me NO₂ CH₂CH₂OMe H 12-132 SO₂Me SO₂Me CH₂CH₂OMe H 12-133 Me Me Me CN 12-134 Me F Me CN 12-135 Me Cl Me CN 12-136 Me Br Me CN 12-137 Me I Me CN 12-138 Me CF₃ Me CN 12-139 Me CHF₂ Me CN 12-140 Me CF₂Cl Me CN 12-141 Me OMe Me CN 12-142 Me NO₂ Me CN 12-143 Me SO₂Me Me CN 12-144 Cl Me Me CN 12-145 Cl F Me CN 12-146 Cl Cl Me CN 12-147 Cl Br Me CN 12-148 Cl I Me CN 12-149 Cl CF₃ Me CN 12-150 Cl CHF₂ Me CN 12-151 Cl CF₂Cl Me CN 12-152 Cl OMe Me CN 12-153 Cl NO₂ Me CN 12-154 Cl SO₂Me Me CN 12-155 OMe Me Me CN 12-156 OMe F Me CN 12-157 OMe Cl Me CN 12-158 OMe Br Me CN 12-159 OMe I Me CN 12-160 OMe CF₃ Me CN 12-161 OMe CHF₂ Me CN 12-162 OMe CF₂Cl Me CN 12-163 OMe OMe Me CN 12-164 OMe NO₂ Me CN 12-165 OMe SO₂Me Me CN 12-166 SO₂Me Me Me CN 12-167 SO₂Me F Me CN 12-168 SO₂Me Cl Me CN 12-169 SO₂Me Br Me CN 12-170 SO₂Me I Me CN 12-171 SO₂Me CF₃ Me CN 12-172 SO₂Me CHF₂ Me CN 12-173 SO₂Me CF₂Cl Me CN 12-174 SO₂Me OMe Me CN 12-175 SO₂Me NO₂ Me CN 12-176 SO₂Me SO₂Me Me CN 12-177 Me Me Et CN 12-178 Me F Et CN 12-179 Me Cl Et CN 12-180 Me Br Et CN 12-181 Me I Et CN 12-182 Me CF₃ Et CN 12-183 Me CHF₂ Et CN 12-184 Me CF₂Cl Et CN 12-185 Me OMe Et CN 12-186 Me NO₂ Et CN 12-187 Me SO₂Me Et CN 12-188 Cl Me Et CN 12-189 Cl F Et CN 12-190 Cl Cl Et CN 12-191 Cl Br Et CN 12-192 Cl I Et CN 12-193 Cl CF₃ Et CN 12-194 Cl CHF₂ Et CN 12-195 Cl CF₂Cl Et CN 12-196 Cl OMe Et CN 12-197 Cl NO₂ Et CN 12-198 Cl SO₂Me Et CN 12-199 OMe Me Et CN 12-200 OMe F Et CN 12-201 OMe Cl Et CN 12-202 OMe Br Et CN 12-203 OMe I Et CN 12-204 OMe CF₃ Et CN 12-205 OMe CHF₂ Et CN 12-206 OMe CF₂Cl Et CN 12-207 OMe OMe Et CN 12-208 OMe NO₂ Et CN 12-209 OMe SO₂Me Et CN 12-210 SO₂Me Me Et CN 12-211 SO₂Me F Et CN 12-212 SO₂Me Cl Et CN 12-213 SO₂Me Br Et CN 12-214 SO₂Me I Et CN 12-215 SO₂Me CF₃ Et CN 12-216 SO₂Me CHF₂ Et CN 12-217 SO₂Me CF₂Cl Et CN 12-218 SO₂Me OMe Et CN 12-219 SO₂Me NO₂ Et CN 12-220 SO₂Me SO₂Me Et CN 12-221 Me Me CH₂CH₂OMe CN 12-222 Me F CH₂CH₂OMe CN 12-223 Me Cl CH₂CH₂OMe CN 12-224 Me Br CH₂CH₂OMe CN 12-225 Me I CH₂CH₂OMe CN 12-226 Me CF₃ CH₂CH₂OMe CN 12-227 Me CHF₂ CH₂CH₂OMe CN 12-228 Me CF₂Cl CH₂CH₂OMe CN 12-229 Me OMe CH₂CH₂OMe CN 12-230 Me NO₂ CH₂CH₂OMe CN 12-231 Me SO₂Me CH₂CH₂OMe CN 12-232 Cl Me CH₂CH₂OMe CN 12-233 Cl F CH₂CH₂OMe CN 12-234 Cl Cl CH₂CH₂OMe CN 12-235 Cl Br CH₂CH₂OMe CN 12-236 Cl I CH₂CH₂OMe CN 12-237 Cl CF₃ CH₂CH₂OMe CN 12-238 Cl CHF₂ CH₂CH₂OMe CN 12-239 Cl CF₂Cl CH₂CH₂OMe CN 12-240 Cl OMe CH₂CH₂OMe CN 12-241 Cl NO₂ CH₂CH₂OMe CN 12-242 Cl SO₂Me CH₂CH₂OMe CN 12-243 OMe Me CH₂CH₂OMe CN 12-244 OMe F CH₂CH₂OMe CN 12-245 OMe Cl CH₂CH₂OMe CN 12-246 OMe Br CH₂CH₂OMe CN 12-247 OMe I CH₂CH₂OMe CN 12-248 OMe CF₃ CH₂CH₂OMe CN 12-249 OMe CHF₂ CH₂CH₂OMe CN 12-250 OMe CF₂Cl CH₂CH₂OMe CN 12-251 OMe OMe CH₂CH₂OMe CN 12-252 OMe NO₂ CH₂CH₂OMe CN 12-253 OMe SO₂Me CH₂CH₂OMe CN 12-254 SO₂Me Me CH₂CH₂OMe CN 12-255 SO₂Me F CH₂CH₂OMe CN 12-256 SO₂Me Cl CH₂CH₂OMe CN 12-257 SO₂Me Br CH₂CH₂OMe CN 12-258 SO₂Me I CH₂CH₂OMe CN 12-259 SO₂Me CF₃ CH₂CH₂OMe CN 12-260 SO₂Me CHF₂ CH₂CH₂OMe CN 12-261 SO₂Me CF₂Cl CH₂CH₂OMe CN 12-262 SO₂Me OMe CH₂CH₂OMe CN 12-263 SO₂Me NO₂ CH₂CH₂OMe CN 12-264 SO₂Me SO₂Me CH₂CH₂OMe CN

TABLE 13 Compounds according to the invention of the formula (I) in which Q is Q5, W is hydrogen, t = 0 and the other radicals have the meanings indicated in the table

No. X Z R R′ Physical data (1H NMR) 13-1 Me Me Me H 13-2 Me F Me H 13-3 Me Cl Me H 13-4 Me Br Me H 13-5 Me I Me H 13-6 Me CF₃ Me H 13-7 Me CHF₂ Me H 13-8 Me CF₂Cl Me H 13-9 Me OMe Me H 13-10 Me NO₂ Me H 13-11 Me SO₂Me Me H 13-12 Cl Me Me H 13-13 Cl F Me H 13-14 Cl Cl Me H 13-15 Cl Br Me H 13-16 Cl I Me H 13-17 Cl CF₃ Me H 13-18 Cl CHF₂ Me H 13-19 Cl CF₂Cl Me H 13-20 Cl OMe Me H 13-21 Cl NO₂ Me H 13-22 Cl SO₂Me Me H 13-23 OMe Me Me H 13-24 OMe F Me H 13-25 OMe Cl Me H 13-26 OMe Br Me H 13-27 OMe I Me H 13-28 OMe CF₃ Me H 13-29 OMe CHF₂ Me H 13-30 OMe CF₂Cl Me H 13-31 OMe OMe Me H 13-32 OMe NO₂ Me H 13-33 OMe SO₂Me Me H 13-34 SO₂Me Me Me H 13-35 SO₂Me F Me H 13-36 SO₂Me Cl Me H 13-37 SO₂Me Br Me H 13-38 SO₂Me I Me H 13-39 SO₂Me CF₃ Me H 13-40 SO₂Me CHF₂ Me H 13-41 SO₂Me CF₂Cl Me H 13-42 SO₂Me OMe Me H 13-43 SO₂Me NO₂ Me H 13-44 SO₂Me SO₂Me Me H 13-45 Me Me Et H 13-46 Me F Et H 13-47 Me Cl Et H 13-48 Me Br Et H 13-49 Me I Et H 13-50 Me CF₃ Et H 13-51 Me CHF₂ Et H 13-52 Me CF₂Cl Et H 13-53 Me OMe Et H 13-54 Me NO₂ Et H 13-55 Me SO₂Me Et H 13-56 Cl Me Et H 13-57 Cl F Et H 13-58 Cl Cl Et H 13-59 Cl Br Et H 13-60 Cl I Et H 13-61 Cl CF₃ Et H 13-62 Cl CHF₂ Et H 13-63 Cl CF₂Cl Et H 13-64 Cl OMe Et H 13-65 Cl NO₂ Et H 13-66 Cl SO₂Me Et H 13-67 OMe Me Et H 13-68 OMe F Et H 13-69 OMe Cl Et H 13-70 OMe Br Et H 13-71 OMe I Et H 13-72 OMe CF₃ Et H 13-73 OMe CHF₂ Et H 13-74 OMe CF₂Cl Et H 13-75 OMe OMe Et H 13-76 OMe NO₂ Et H 13-77 OMe SO₂Me Et H 13-78 SO₂Me Me Et H 13-79 SO₂Me F Et H 13-80 SO₂Me Cl Et H 13-81 SO₂Me Br Et H 13-82 SO₂Me I Et H 13-83 SO₂Me CF₃ Et H 13-84 SO₂Me CHF₂ Et H 13-85 SO₂Me CF₂Cl Et H 13-86 SO₂Me OMe Et H 13-87 SO₂Me NO₂ Et H 13-88 SO₂Me SO₂Me Et H 13-89 Me Me CH₂CH₂OMe H 13-90 Me F CH₂CH₂OMe H 13-91 Me Cl CH₂CH₂OMe H 13-92 Me Br CH₂CH₂OMe H 13-93 Me I CH₂CH₂OMe H 13-94 Me CF₃ CH₂CH₂OMe H 13-95 Me CHF₂ CH₂CH₂OMe H 13-96 Me CF₂Cl CH₂CH₂OMe H 13-97 Me OMe CH₂CH₂OMe H 13-98 Me NO₂ CH₂CH₂OMe H 13-99 Me SO₂Me CH₂CH₂OMe H 13-100 Cl Me CH₂CH₂OMe H 13-101 Cl F CH₂CH₂OMe H 13-102 Cl Cl CH₂CH₂OMe H 13-103 Cl Br CH₂CH₂OMe H 13-104 Cl I CH₂CH₂OMe H 13-105 Cl CF₃ CH₂CH₂OMe H 13-106 Cl CHF₂ CH₂CH₂OMe H 13-107 Cl CF₂Cl CH₂CH₂OMe H 13-108 Cl OMe CH₂CH₂OMe H 13-109 Cl NO₂ CH₂CH₂OMe H 13-110 Cl SO₂Me CH₂CH₂OMe H 13-111 OMe Me CH₂CH₂OMe H 13-112 OMe F CH₂CH₂OMe H 13-113 OMe Cl CH₂CH₂OMe H 13-114 OMe Br CH₂CH₂OMe H 13-115 OMe I CH₂CH₂OMe H 13-116 OMe CF₃ CH₂CH₂OMe H 13-117 OMe CHF₂ CH₂CH₂OMe H 13-118 OMe CF₂Cl CH₂CH₂OMe H 13-119 OMe OMe CH₂CH₂OMe H 13-120 OMe NO₂ CH₂CH₂OMe H 13-121 OMe SO₂Me CH₂CH₂OMe H 13-122 SO₂Me Me CH₂CH₂OMe H 13-123 SO₂Me F CH₂CH₂OMe H 13-124 SO₂Me Cl CH₂CH₂OMe H 13-125 SO₂Me Br CH₂CH₂OMe H 13-126 SO₂Me I CH₂CH₂OMe H 13-127 SO₂Me CF₃ CH₂CH₂OMe H 13-128 SO₂Me CHF₂ CH₂CH₂OMe H 13-129 SO₂Me CF₂Cl CH₂CH₂OMe H 13-130 SO₂Me OMe CH₂CH₂OMe H 13-131 SO₂Me NO₂ CH₂CH₂OMe H 13-132 SO₂Me SO₂Me CH₂CH₂OMe H 13-133 Me Me Me CN 13-134 Me F Me CN 13-135 Me Cl Me CN 13-136 Me Br Me CN 13-137 Me I Me CN 13-138 Me CF₃ Me CN 13-139 Me CHF₂ Me CN 13-140 Me CF₂Cl Me CN 13-141 Me OMe Me CN 13-142 Me NO₂ Me CN 13-143 Me SO₂Me Me CN 13-144 Cl Me Me CN 13-145 Cl F Me CN 13-146 Cl Cl Me CN 13-147 Cl Br Me CN 13-148 Cl I Me CN 13-149 Cl CF₃ Me CN 13-150 Cl CHF₂ Me CN 13-151 Cl CF₂Cl Me CN 13-152 Cl OMe Me CN 13-153 Cl NO₂ Me CN 13-154 Cl SO₂Me Me CN 13-155 OMe Me Me CN 13-156 OMe F Me CN 13-157 OMe Cl Me CN 13-158 OMe Br Me CN 13-159 OMe I Me CN 13-160 OMe CF₃ Me CN 13-161 OMe CHF₂ Me CN 13-162 OMe CF₂Cl Me CN 13-163 OMe OMe Me CN 13-164 OMe NO₂ Me CN 13-165 OMe SO₂Me Me CN 13-166 SO₂Me Me Me CN 13-167 SO₂Me F Me CN 13-168 SO₂Me Cl Me CN 13-169 SO₂Me Br Me CN 13-170 SO₂Me I Me CN 13-171 SO₂Me CF₃ Me CN 13-172 SO₂Me CHF₂ Me CN 13-173 SO₂Me CF₂Cl Me CN 13-174 SO₂Me OMe Me CN 13-175 SO₂Me NO₂ Me CN 13-176 SO₂Me SO₂Me Me CN 13-177 Me Me Et CN 13-178 Me F Et CN 13-179 Me Cl Et CN 13-180 Me Br Et CN 13-181 Me I Et CN 13-182 Me CF₃ Et CN 13-183 Me CHF₂ Et CN 13-184 Me CF₂Cl Et CN 13-185 Me OMe Et CN 13-186 Me NO₂ Et CN 13-187 Me SO₂Me Et CN 13-188 Cl Me Et CN 13-189 Cl F Et CN 13-190 Cl Cl Et CN 13-191 Cl Br Et CN 13-192 Cl I Et CN 13-193 Cl CF₃ Et CN 13-194 Cl CHF₂ Et CN 13-195 Cl CF₂Cl Et CN 13-196 Cl OMe Et CN 13-197 Cl NO₂ Et CN 13-198 Cl SO₂Me Et CN 13-199 OMe Me Et CN 13-200 OMe F Et CN 13-201 OMe Cl Et CN 13-202 OMe Br Et CN 13-203 OMe I Et CN 13-204 OMe CF₃ Et CN 13-205 OMe CHF₂ Et CN 13-206 OMe CF₂Cl Et CN 13-207 OMe OMe Et CN 13-208 OMe NO₂ Et CN 13-209 OMe SO₂Me Et CN 13-210 SO₂Me Me Et CN 13-211 SO₂Me F Et CN 13-212 SO₂Me Cl Et CN 13-213 SO₂Me Br Et CN 13-214 SO₂Me I Et CN 13-215 SO₂Me CF₃ Et CN 13-216 SO₂Me CHF₂ Et CN 13-217 SO₂Me CF₂Cl Et CN 13-218 SO₂Me OMe Et CN 13-219 SO₂Me NO₂ Et CN 13-220 SO₂Me SO₂Me Et CN 13-221 Me Me CH₂CH₂OMe CN 13-222 Me F CH₂CH₂OMe CN 13-223 Me Cl CH₂CH₂OMe CN 13-224 Me Br CH₂CH₂OMe CN 13-225 Me I CH₂CH₂OMe CN 13-226 Me CF₃ CH₂CH₂OMe CN 13-227 Me CHF₂ CH₂CH₂OMe CN 13-228 Me CF₂Cl CH₂CH₂OMe CN 13-229 Me OMe CH₂CH₂OMe CN 13-230 Me NO₂ CH₂CH₂OMe CN 13-231 Me SO₂Me CH₂CH₂OMe CN 13-232 Cl Me CH₂CH₂OMe CN 13-233 Cl F CH₂CH₂OMe CN 13-234 Cl Cl CH₂CH₂OMe CN 13-235 Cl Br CH₂CH₂OMe CN 13-236 Cl I CH₂CH₂OMe CN 13-237 Cl CF₃ CH₂CH₂OMe CN 13-238 Cl CHF₂ CH₂CH₂OMe CN 13-239 Cl CF₂Cl CH₂CH₂OMe CN 13-240 Cl OMe CH₂CH₂OMe CN 13-241 Cl NO₂ CH₂CH₂OMe CN 13-242 Cl SO₂Me CH₂CH₂OMe CN 13-243 OMe Me CH₂CH₂OMe CN 13-244 OMe F CH₂CH₂OMe CN 13-245 OMe Cl CH₂CH₂OMe CN 13-246 OMe Br CH₂CH₂OMe CN 13-247 OMe I CH₂CH₂OMe CN 13-248 OMe CF₃ CH₂CH₂OMe CN 13-249 OMe CHF₂ CH₂CH₂OMe CN 13-250 OMe CF₂Cl CH₂CH₂OMe CN 13-251 OMe OMe CH₂CH₂OMe CN 13-252 OMe NO₂ CH₂CH₂OMe CN 13-253 OMe SO₂Me CH₂CH₂OMe CN 13-254 SO₂Me Me CH₂CH₂OMe CN 13-255 SO₂Me F CH₂CH₂OMe CN 13-256 SO₂Me Cl CH₂CH₂OMe CN 13-257 SO₂Me Br CH₂CH₂OMe CN 13-258 SO₂Me I CH₂CH₂OMe CN 13-259 SO₂Me CF₃ CH₂CH₂OMe CN 13-260 SO₂Me CHF₂ CH₂CH₂OMe CN 13-261 SO₂Me CF₂Cl CH₂CH₂OMe CN 13-262 SO₂Me OMe CH₂CH₂OMe CN 13-263 SO₂Me NO₂ CH₂CH₂OMe CN 13-264 SO₂Me SO₂Me CH₂CH₂OMe CN

TABLE 14 Compounds according to the invention of the formula (I) in the form of the sodium salts in which Q is Q3, R^(i) is methyl, R^(k) and W are each hydrogen, t = 0 and the other radicals have the meanings indicated in the table

No. X Z R R′ Physical data (1H NMR) 14-1 Me Me Me H 14-2 Me Cl Me H 14-3 Me CF₃ Me H 14-4 Me CHF₂ Me H 14-5 Cl Me Me H 14-6 Cl Cl Me H 14-7 Cl CF₃ Me H 14-8 Cl CHF₂ Me H 14-9 OMe Me Me H 14-10 OMe Cl Me H 14-11 OMe CF₃ Me H 14-12 OMe CHF₂ Me H 14-13 SO₂Me Me Me H 14-14 SO₂Me Cl Me H 14-15 SO₂Me CF₃ Me H 14-16 SO₂Me CHF₂ Me H 14-17 Me Me Et H 14-18 Me Cl Et H 14-19 Me CF₃ Et H 14-20 Me CHF₂ Et H 14-21 Cl Me Et H 14-22 Cl Cl Et H 14-23 Cl CF₃ Et H 14-24 Cl CHF₂ Et H 14-25 OMe Me Et H 14-26 OMe Cl Et H 14-27 OMe CF₃ Et H 14-28 OMe CHF₂ Et H 14-29 SO₂Me Me Et H 14-30 SO₂Me Cl Et H 14-31 SO₂Me CF₃ Et H 14-32 SO₂Me CHF₂ Et H 14-33 Me Me CH₂CH₂OMe H 14-34 Me Cl CH₂CH₂OMe H 14-35 Me CF₃ CH₂CH₂OMe H 14-36 Me CHF₂ CH₂CH₂OMe H 14-37 Cl Me CH₂CH₂OMe H 14-38 Cl Cl CH₂CH₂OMe H 14-39 Cl CF₃ CH₂CH₂OMe H 14-40 Cl CHF₂ CH₂CH₂OMe H 14-41 OMe Me CH₂CH₂OMe H 14-42 OMe Cl CH₂CH₂OMe H 14-43 OMe CF₃ CH₂CH₂OMe H 14-44 OMe CHF₂ CH₂CH₂OMe H 14-45 SO₂Me Me CH₂CH₂OMe H 14-46 SO₂Me Cl CH₂CH₂OMe H 14-47 SO₂Me CF₃ CH₂CH₂OMe H 14-48 SO₂Me CHF₂ CH₂CH₂OMe H 14-49 Me Me Me CN 14-50 Me Cl Me CN 14-51 Me CF₃ Me CN 14-52 Me CHF₂ Me CN 14-53 Cl Me Me CN 14-54 Cl Cl Me CN 14-55 Cl CF₃ Me CN 14-56 Cl CHF₂ Me CN 14-57 OMe Me Me CN 14-58 OMe Cl Me CN 14-59 OMe CF₃ Me CN 14-60 OMe CHF₂ Me CN 14-61 SO₂Me Me Me CN 14-62 SO₂Me Cl Me CN 14-63 SO₂Me CF₃ Me CN 14-64 SO₂Me CHF₂ Me CN 14-65 Me Me Et CN 14-66 Me Cl Et CN 14-67 Me CF₃ Et CN 14-68 Me CHF₂ Et CN 14-69 Cl Me Et CN 14-70 Cl Cl Et CN 14-71 Cl CF₃ Et CN 14-72 Cl CHF₂ Et CN 14-73 OMe Me Et CN 14-74 OMe Cl Et CN 14-75 OMe CF₃ Et CN 14-76 OMe CHF₂ Et CN 14-77 SO₂Me Me Et CN 14-78 SO₂Me Cl Et CN 14-79 SO₂Me CF₃ Et CN 14-80 SO₂Me CHF₂ Et CN 14-81 Me Me CH₂CH₂OMe CN 14-82 Me Cl CH₂CH₂OMe CN 14-83 Me CF₃ CH₂CH₂OMe CN 14-84 Me CHF₂ CH₂CH₂OMe CN 14-85 Cl Me CH₂CH₂OMe CN 14-86 Cl Cl CH₂CH₂OMe CN 14-87 Cl CF₃ CH₂CH₂OMe CN 14-88 Cl CHF₂ CH₂CH₂OMe CN 14-89 OMe Me CH₂CH₂OMe CN 14-90 OMe Cl CH₂CH₂OMe CN 14-91 OMe CF₃ CH₂CH₂OMe CN 14-92 OMe CHF₂ CH₂CH₂OMe CN 14-93 SO₂Me Me CH₂CH₂OMe CN 14-94 SO₂Me Cl CH₂CH₂OMe CN 14-95 SO₂Me CF₃ CH₂CH₂OMe CN 14-96 SO₂Me CHF₂ CH₂CH₂OMe CN

TABLE 15 Compounds according to the invention of the formula (II) in which Q* is hydroxyl and R′ is cyano, t is 1, and the other radicals have the meanings indicated in the table

No. X Z R Physical data (¹H NMR) 15-1 Me Me Me 15-2 Me F Me 15-3 Me Cl Me 15-4 Me Br Me 15-5 Me I Me 15-6 Me CF₃ Me 15-7 Me CHF₂ Me 15-8 Me CF₂Cl Me 15-9 Me OMe Me 15-10 Me NO₂ Me 15-11 Me SO₂Me Me 15-12 Cl Me Me 15-13 Cl F Me 15-14 Cl Cl Me 15-15 Cl Br Me 15-16 Cl I Me 15-17 Cl CF₃ Me 15-18 Cl CHF₂ Me 15-19 Cl CF₂Cl Me 15-20 Cl OMe Me 15-21 Cl NO₂ Me 15-22 Cl SO₂Me Me 15-23 OMe Me Me 15-24 OMe F Me 15-25 OMe Cl Me 15-26 OMe Br Me 15-27 OMe I Me 15-28 OMe CF₃ Me (400 MHz, CDCl₃ δ, ppm) 8.34 (d, 1H), 7.84 (d, 1H), 4.16 (s, 3H), 3.68 (s, 3H) 15-29 OMe CHF₂ Me 15-30 OMe CF₂Cl Me 15-31 OMe OMe Me 15-32 OMe NO₂ Me 15-33 OMe SO₂Me Me 15-34 SO₂Me Me Me 15-35 SO₂Me F Me 15-36 SO₂Me Cl Me 15-37 SO₂Me Br Me 15-38 SO₂Me I Me 15-39 SO₂Me CF₃ Me 15-40 SO₂Me CHF₂ Me 15-41 SO₂Me CF₂Cl Me 15-42 SO₂Me OMe Me 15-43 SO₂Me NO₂ Me 15-44 SO₂Me SO₂Me Me 15-45 Me Me Et 15-46 Me F Et 15-47 Me Cl Et 15-48 Me Br Et 15-49 Me I Et 15-50 Me CF₃ Et 15-51 Me CHF₂ Et 15-52 Me CF₂Cl Et 15-53 Me OMe Et 15-54 Me NO₂ Et 15-55 Me SO₂Me Et 15-56 Cl Me Et 15-57 Cl F Et 15-58 Cl Cl Et 15-59 Cl Br Et 15-60 Cl I Et 15-61 Cl CF₃ Et 15-62 Cl CHF₂ Et 15-63 Cl CF₂Cl Et 15-64 Cl OMe Et 15-65 Cl NO₂ Et 15-66 Cl SO₂Me Et 15-67 OMe Me Et 15-68 OMe F Et 15-69 OMe Cl Et 15-70 OMe Br Et 15-71 OMe I Et 15-72 OMe CF₃ Et 15-73 OMe CHF₂ Et 15-74 OMe CF₂Cl Et 15-75 OMe OMe Et 15-76 OMe NO₂ Et 15-77 OMe SO₂Me Et 15-78 SO₂Me Me Et 15-79 SO₂Me F Et 15-80 SO₂Me Cl Et 15-81 SO₂Me Br Et 15-82 SO₂Me I Et 15-83 SO₂Me CF₃ Et 15-84 SO₂Me CHF₂ Et 15-85 SO₂Me CF₂Cl Et 15-86 SO₂Me OMe Et 15-87 SO₂Me NO₂ Et 15-88 SO₂Me SO₂Me Et 15-89 Me Me CH₂CH₂OMe 15-90 Me F CH₂CH₂OMe 15-91 Me Cl CH₂CH₂OMe 15-92 Me Br CH₂CH₂OMe 15-93 Me I CH₂CH₂OMe 15-94 Me CF₃ CH₂CH₂OMe 15-95 Me CHF₂ CH₂CH₂OMe 15-96 Me CF₂Cl CH₂CH₂OMe 15-97 Me OMe CH₂CH₂OMe 15-98 Me NO₂ CH₂CH₂OMe 15-99 Me SO₂Me CH₂CH₂OMe 15-100 Cl Me CH₂CH₂OMe 15-101 Cl F CH₂CH₂OMe 15-102 Cl Cl CH₂CH₂OMe 15-103 Cl Br CH₂CH₂OMe 15-104 Cl I CH₂CH₂OMe 15-105 Cl CF₃ CH₂CH₂OMe 15-106 Cl CHF₂ CH₂CH₂OMe 15-107 Cl CF₂Cl CH₂CH₂OMe 15-108 Cl OMe CH₂CH₂OMe 15-109 Cl NO₂ CH₂CH₂OMe 15-110 Cl SO₂Me CH₂CH₂OMe 15-111 OMe Me CH₂CH₂OMe 15-112 OMe F CH₂CH₂OMe 15-113 OMe Cl CH₂CH₂OMe 15-114 OMe Br CH₂CH₂OMe 15-115 OMe I CH₂CH₂OMe 15-116 OMe CF₃ CH₂CH₂OMe 15-117 OMe CHF₂ CH₂CH₂OMe 15-118 OMe CF₂Cl CH₂CH₂OMe 15-119 OMe OMe CH₂CH₂OMe 15-120 OMe NO₂ CH₂CH₂OMe 15-121 OMe SO₂Me CH₂CH₂OMe 15-122 SO₂Me Me CH₂CH₂OMe 15-123 SO₂Me F CH₂CH₂OMe 15-124 SO₂Me Cl CH₂CH₂OMe 15-125 SO₂Me Br CH₂CH₂OMe 15-126 SO₂Me I CH₂CH₂OMe 15-127 SO₂Me CF₃ CH₂CH₂OMe 15-128 SO₂Me CHF₂ CH₂CH₂OMe 15-129 SO₂Me CF₂Cl CH₂CH₂OMe 15-130 SO₂Me OMe CH₂CH₂OMe 15-131 SO₂Me NO₂ CH₂CH₂OMe 15-132 SO₂Me SO₂Me CH₂CH₂OMe

TABLE 16 Compounds according to the invention of the formula (II) in which Q* is hydroxyl and R′ is cyano, t is 0, and the other radicals have the meanings indicated in the table

No. X Z R Physical data (¹H NMR) 16-1 Me Me Me 16-2 Me F Me 16-3 Me Cl Me 16-4 Me Br Me 16-5 Me I Me 16-6 Me CF₃ Me 16-7 Me CHF₂ Me 16-8 Me CF₂Cl Me 16-9 Me OMe Me 16-10 Me NO₂ Me 16-11 Me SO₂Me Me 16-12 Cl Me Me 16-13 Cl F Me 16-14 Cl Cl Me 16-15 Cl Br Me 16-16 Cl I Me 16-17 Cl CF₃ Me 16-18 Cl CHF₂ Me 16-19 Cl CF₂Cl Me 16-20 Cl OMe Me 16-21 Cl NO₂ Me 16-22 Cl SO₂Me Me 16-23 OMe Me Me 16-24 OMe F Me 16-25 OMe Cl Me 16-26 OMe Br Me 16-27 OMe I Me 16-28 OMe CF₃ Me 16-29 OMe CHF₂ Me 16-30 OMe CF₂Cl Me 16-31 OMe OMe Me 16-32 OMe NO₂ Me 16-33 OMe SO₂Me Me 16-34 SO₂Me Me Me 16-35 SO₂Me F Me 16-36 SO₂Me Cl Me 16-37 SO₂Me Br Me 16-38 SO₂Me I Me 16-39 SO₂Me CF₃ Me 16-40 SO₂Me CHF₂ Me 16-41 SO₂Me CF₂Cl Me 16-42 SO₂Me OMe Me 16-43 SO₂Me NO₂ Me 16-44 SO₂Me SO₂Me Me 16-45 Me Me Et 16-46 Me F Et 16-47 Me Cl Et 16-48 Me Br Et 16-49 Me I Et 16-50 Me CF₃ Et 16-51 Me CHF₂ Et 16-52 Me CF₂Cl Et 16-53 Me OMe Et 16-54 Me NO₂ Et 16-55 Me SO₂Me Et 16-56 Cl Me Et 16-57 Cl F Et 16-58 Cl Cl Et 16-59 Cl Br Et 16-60 Cl I Et 16-61 Cl CF₃ Et 16-62 Cl CHF₂ Et 16-63 Cl CF₂Cl Et 16-64 Cl OMe Et 16-65 Cl NO₂ Et 16-66 Cl SO₂Me Et 16-67 OMe Me Et 16-68 OMe F Et 16-69 OMe Cl Et 16-70 OMe Br Et 16-71 OMe I Et 16-72 OMe CF₃ Et 16-73 OMe CHF₂ Et 16-74 OMe CF₂Cl Et 16-75 OMe OMe Et 16-76 OMe NO₂ Et 16-77 OMe SO₂Me Et 16-78 SO₂Me Me Et 16-79 SO₂Me F Et 16-80 SO₂Me Cl Et 16-81 SO₂Me Br Et 16-82 SO₂Me I Et 16-83 SO₂Me CF₃ Et 16-84 SO₂Me CHF₂ Et 16-85 SO₂Me CF₂Cl Et 16-86 SO₂Me OMe Et 16-87 SO₂Me NO₂ Et 16-88 SO₂Me SO₂Me Et 16-89 Me Me CH₂CH₂OMe 16-90 Me F CH₂CH₂OMe 16-91 Me Cl CH₂CH₂OMe 16-92 Me Br CH₂CH₂OMe 16-93 Me I CH₂CH₂OMe 16-94 Me CF₃ CH₂CH₂OMe 16-95 Me CHF₂ CH₂CH₂OMe 16-96 Me CF₂Cl CH₂CH₂OMe 16-97 Me OMe CH₂CH₂OMe 16-98 Me NO₂ CH₂CH₂OMe 16-99 Me SO₂Me CH₂CH₂OMe 16-100 Cl Me CH₂CH₂OMe 16-101 Cl F CH₂CH₂OMe 16-102 Cl Cl CH₂CH₂OMe 16-103 Cl Br CH₂CH₂OMe 16-104 Cl I CH₂CH₂OMe 16-105 Cl CF₃ CH₂CH₂OMe 16-106 Cl CHF₂ CH₂CH₂OMe 16-107 Cl CF₂Cl CH₂CH₂OMe 16-108 Cl OMe CH₂CH₂OMe 16-109 Cl NO₂ CH₂CH₂OMe 16-110 Cl SO₂Me CH₂CH₂OMe 16-111 OMe Me CH₂CH₂OMe 16-112 OMe F CH₂CH₂OMe 16-113 OMe Cl CH₂CH₂OMe 16-114 OMe Br CH₂CH₂OMe 16-115 OMe I CH₂CH₂OMe 16-116 OMe CF₃ CH₂CH₂OMe 16-117 OMe CHF₂ CH₂CH₂OMe 16-118 OMe CF₂Cl CH₂CH₂OMe 16-119 OMe OMe CH₂CH₂OMe 16-120 OMe NO₂ CH₂CH₂OMe 16-121 OMe SO₂Me CH₂CH₂OMe 16-122 SO₂Me Me CH₂CH₂OMe 16-123 SO₂Me F CH₂CH₂OMe 16-124 SO₂Me Cl CH₂CH₂OMe 16-125 SO₂Me Br CH₂CH₂OMe 16-126 SO₂Me I CH₂CH₂OMe 16-127 SO₂Me CF₃ CH₂CH₂OMe 16-128 SO₂Me CHF₂ CH₂CH₂OMe 16-129 SO₂Me CF₂Cl CH₂CH₂OMe 16-130 SO₂Me OMe CH₂CH₂OMe 16-131 SO₂Me NO₂ CH₂CH₂OMe 16-132 SO₂Me SO₂Me CH₂CH₂OMe

TABLE 17 Compounds according to the invention of the formula (II) in which Q* is chlorine and R′ is cyano, t is 1, and the other radicals have the meanings indicated in the table

No. X Z R Physical data (¹H NMR) 17-1 Me Me Me 17-2 Me F Me 17-3 Me Cl Me 17-4 Me Br Me 17-5 Me I Me 17-6 Me CF₃ Me 17-7 Me CHF₂ Me 17-8 Me CF₂Cl Me 17-9 Me OMe Me 17-10 Me NO₂ Me 17-11 Me SO₂Me Me 17-12 Cl Me Me 17-13 Cl F Me 17-14 Cl Cl Me 17-15 Cl Br Me 17-16 Cl I Me 17-17 Cl CF₃ Me 17-18 Cl CHF₂ Me 17-19 Cl CF₂Cl Me 17-20 Cl OMe Me 17-21 Cl NO₂ Me 17-22 Cl SO₂Me Me 17-23 OMe Me Me 17-24 OMe F Me 17-25 OMe Cl Me 17-26 OMe Br Me 17-27 OMe I Me 17-28 OMe CF₃ Me 17-29 OMe CHF₂ Me 17-30 OMe CF₂Cl Me 17-31 OMe OMe Me 17-32 OMe NO₂ Me 17-33 OMe SO₂Me Me 17-34 SO₂Me Me Me 17-35 SO₂Me F Me 17-36 SO₂Me Cl Me 17-37 SO₂Me Br Me 17-38 SO₂Me I Me 17-39 SO₂Me CF₃ Me 17-40 SO₂Me CHF₂ Me 17-41 SO₂Me CF₂Cl Me 17-42 SO₂Me OMe Me 17-43 SO₂Me NO₂ Me 17-44 SO₂Me SO₂Me Me 17-45 Me Me Et 17-46 Me F Et 17-47 Me Cl Et 17-48 Me Br Et 17-49 Me I Et 17-50 Me CF₃ Et 17-51 Me CHF₂ Et 17-52 Me CF₂Cl Et 17-53 Me OMe Et 17-54 Me NO₂ Et 17-55 Me SO₂Me Et 17-56 Cl Me Et 17-57 Cl F Et 17-58 Cl Cl Et 17-59 Cl Br Et 17-60 Cl I Et 17-61 Cl CF₃ Et 17-62 Cl CHF₂ Et 17-63 Cl CF₂Cl Et 17-64 Cl OMe Et 17-65 Cl NO₂ Et 17-66 Cl SO₂Me Et 17-67 OMe Me Et 17-68 OMe F Et 17-69 OMe Cl Et 17-70 OMe Br Et 17-71 OMe I Et 17-72 OMe CF₃ Et 17-73 OMe CHF₂ Et 17-74 OMe CF₂Cl Et 17-75 OMe OMe Et 17-76 OMe NO₂ Et 17-77 OMe SO₂Me Et 17-78 SO₂Me Me Et 17-79 SO₂Me F Et 17-80 SO₂Me Cl Et 17-81 SO₂Me Br Et 17-82 SO₂Me I Et 17-83 SO₂Me CF₃ Et 17-84 SO₂Me CHF₂ Et 17-85 SO₂Me CF₂Cl Et 17-86 SO₂Me OMe Et 17-87 SO₂Me NO₂ Et 17-88 SO₂Me SO₂Me Et 17-89 Me Me CH₂CH₂OMe 17-90 Me F CH₂CH₂OMe 17-91 Me Cl CH₂CH₂OMe 17-92 Me Br CH₂CH₂OMe 17-93 Me I CH₂CH₂OMe 17-94 Me CF₃ CH₂CH₂OMe 17-95 Me CHF₂ CH₂CH₂OMe 17-96 Me CF₂Cl CH₂CH₂OMe 17-97 Me OMe CH₂CH₂OMe 17-98 Me NO₂ CH₂CH₂OMe 17-99 Me SO₂Me CH₂CH₂OMe 17-100 Cl Me CH₂CH₂OMe 17-101 Cl F CH₂CH₂OMe 17-102 Cl Cl CH₂CH₂OMe 17-103 Cl Br CH₂CH₂OMe 17-104 Cl I CH₂CH₂OMe 17-105 Cl CF₃ CH₂CH₂OMe 17-106 Cl CHF₂ CH₂CH₂OMe 17-107 Cl CF₂Cl CH₂CH₂OMe 17-108 Cl OMe CH₂CH₂OMe 17-109 Cl NO₂ CH₂CH₂OMe 17-110 Cl SO₂Me CH₂CH₂OMe 17-111 OMe Me CH₂CH₂OMe 17-112 OMe F CH₂CH₂OMe 17-113 OMe Cl CH₂CH₂OMe 17-114 OMe Br CH₂CH₂OMe 17-115 OMe I CH₂CH₂OMe 17-116 OMe CF₃ CH₂CH₂OMe 17-117 OMe CHF₂ CH₂CH₂OMe 17-118 OMe CF₂Cl CH₂CH₂OMe 17-119 OMe OMe CH₂CH₂OMe 17-120 OMe NO₂ CH₂CH₂OMe 17-121 OMe SO₂Me CH₂CH₂OMe 17-122 SO₂Me Me CH₂CH₂OMe 17-123 SO₂Me F CH₂CH₂OMe 17-124 SO₂Me Cl CH₂CH₂OMe 17-125 SO₂Me Br CH₂CH₂OMe 17-126 SO₂Me I CH₂CH₂OMe 17-127 SO₂Me CF₃ CH₂CH₂OMe 17-128 SO₂Me CHF₂ CH₂CH₂OMe 17-129 SO₂Me CF₂Cl CH₂CH₂OMe 17-130 SO₂Me OMe CH₂CH₂OMe 17-131 SO₂Me NO₂ CH₂CH₂OMe 17-132 SO₂Me SO₂Me CH₂CH₂OMe

TABLE 18 Compounds accordng to the invention of the formula (II) in which Q* is chlorine and R′ is cyano, t is 0, and the other radicals have the meanings indicated in the table

No. X Z R Physical data (¹H NMR) 18-1 Me Me Me 18-2 Me F Me 18-3 Me Cl Me 18-4 Me Br Me 18-5 Me I Me 18-6 Me CF₃ Me 18-7 Me CHF₂ Me 18-8 Me CF₂Cl Me 18-9 Me OMe Me 18-10 Me NO₂ Me 18-11 Me SO₂Me Me 18-12 Cl Me Me 18-13 Cl F Me 18-14 Cl Cl Me 18-15 Cl Br Me 18-16 Cl I Me 18-17 Cl CF₃ Me 18-18 Cl CHF₂ Me 18-19 Cl CF₂Cl Me 18-20 Cl OMe Me 18-21 Cl NO₂ Me 18-22 Cl SO₂Me Me 18-23 OMe Me Me 18-24 OMe F Me 18-25 OMe Cl Me 18-26 OMe Br Me 18-27 OMe I Me 18-28 OMe CF₃ Me 18-29 OMe CHF₂ Me 18-30 OMe CF₂Cl Me 18-31 OMe OMe Me 18-32 OMe NO₂ Me 18-33 OMe SO₂Me Me 18-34 SO₂Me Me Me 18-35 SO₂Me F Me 18-36 SO₂Me Cl Me 18-37 SO₂Me Br Me 18-38 SO₂Me I Me 18-39 SO₂Me CF₃ Me 18-40 SO₂Me CHF₂ Me 18-41 SO₂Me CF₂Cl Me 18-42 SO₂Me OMe Me 18-43 SO₂Me NO₂ Me 18-44 SO₂Me SO₂Me Me 18-45 Me Me Et 18-46 Me F Et 18-47 Me Cl Et 18-48 Me Br Et 18-49 Me I Et 18-50 Me CF₃ Et 18-51 Me CHF₂ Et 18-52 Me CF₂Cl Et 18-53 Me OMe Et 18-54 Me NO₂ Et 18-55 Me SO₂Me Et 18-56 Cl Me Et 18-57 Cl F Et 18-58 Cl Cl Et 18-59 Cl Br Et 18-60 Cl I Et 18-61 Cl CF₃ Et 18-62 Cl CHF₂ Et 18-63 Cl CF₂Cl Et 18-64 Cl OMe Et 18-65 Cl NO₂ Et 18-66 Cl SO₂Me Et 18-67 OMe Me Et 18-68 OMe F Et 18-69 OMe Cl Et 18-70 OMe Br Et 18-71 OMe I Et 18-72 OMe CF₃ Et 18-73 OMe CHF₂ Et 18-74 OMe CF₂Cl Et 18-75 OMe OMe Et 18-76 OMe NO₂ Et 18-77 OMe SO₂Me Et 18-78 SO₂Me Me Et 18-79 SO₂Me F Et 18-80 SO₂Me Cl Et 18-81 SO₂Me Br Et 18-82 SO₂Me I Et 18-83 SO₂Me CF₃ Et 18-84 SO₂Me CHF₂ Et 18-85 SO₂Me CF₂Cl Et 18-86 SO₂Me OMe Et 18-87 SO₂Me NO₂ Et 18-88 SO₂Me SO₂Me Et 18-89 Me Me CH₂CH₂OMe 18-90 Me F CH₂CH₂OMe 18-91 Me Cl CH₂CH₂OMe 18-92 Me Br CH₂CH₂OMe 18-93 Me I CH₂CH₂OMe 18-94 Me CF₃ CH₂CH₂OMe 18-95 Me CHF₂ CH₂CH₂OMe 18-96 Me CF₂Cl CH₂CH₂OMe 18-97 Me OMe CH₂CH₂OMe 18-98 Me NO₂ CH₂CH₂OMe 18-99 Me SO₂Me CH₂CH₂OMe 18-100 Cl Me CH₂CH₂OMe 18-101 Cl F CH₂CH₂OMe 18-102 Cl Cl CH₂CH₂OMe 18-103 Cl Br CH₂CH₂OMe 18-104 Cl I CH₂CH₂OMe 18-105 Cl CF₃ CH₂CH₂OMe 18-106 Cl CHF₂ CH₂CH₂OMe 18-107 Cl CF₂Cl CH₂CH₂OMe 18-108 Cl OMe CH₂CH₂OMe 18-109 Cl NO₂ CH₂CH₂OMe 18-110 Cl SO₂Me CH₂CH₂OMe 18-111 OMe Me CH₂CH₂OMe 18-112 OMe F CH₂CH₂OMe 18-113 OMe Cl CH₂CH₂OMe 18-114 OMe Br CH₂CH₂OMe 18-115 OMe I CH₂CH₂OMe 18-116 OMe CF₃ CH₂CH₂OMe 18-117 OMe CHF₂ CH₂CH₂OMe 18-118 OMe CF₂Cl CH₂CH₂OMe 18-119 OMe OMe CH₂CH₂OMe 18-120 OMe NO₂ CH₂CH₂OMe 18-121 OMe SO₂Me CH₂CH₂OMe 18-122 SO₂Me Me CH₂CH₂OMe 18-123 SO₂Me F CH₂CH₂OMe 18-124 SO₂Me Cl CH₂CH₂OMe 18-125 SO₂Me Br CH₂CH₂OMe 18-126 SO₂Me I CH₂CH₂OMe 18-127 SO₂Me CF₃ CH₂CH₂OMe 18-128 SO₂Me CHF₂ CH₂CH₂OMe 18-129 SO₂Me CF₂Cl CH₂CH₂OMe 18-130 SO₂Me OMe CH₂CH₂OMe 18-131 SO₂Me NO₂ CH₂CH₂OMe 18-132 SO₂Me SO₂Me CH₂CH₂OMe

TABLE 19 Compounds according to the invention of the formula (II) in which Q* is methoxy and R′ is cyano, t is 1, and the other radicals have the meanings indicated in the table

No. X Z R Physical data (¹H NMR) 19-1 Me Me Me 19-2 Me F Me 19-3 Me Cl Me 19-4 Me Br Me 19-5 Me I Me 19-6 Me CF₃ Me 19-7 Me CHF₂ Me 19-8 Me CF₂Cl Me 19-9 Me OMe Me 19-10 Me NO₂ Me 19-11 Me SO₂Me Me 19-12 Cl Me Me 19-13 Cl F Me 19-14 Cl Cl Me 19-15 Cl Br Me 19-16 Cl I Me 19-17 Cl CF₃ Me 19-18 Cl CHF₂ Me 19-19 Cl CF₂Cl Me 19-20 Cl OMe Me 19-21 Cl NO₂ Me 19-22 Cl SO₂Me Me 19-23 OMe Me Me 19-24 OMe F Me 19-25 OMe Cl Me 19-26 OMe Br Me 19-27 OMe I Me 19-28 OMe CF₃ Me 19-29 OMe CHF₂ Me 19-30 OMe CF₂Cl Me 19-31 OMe OMe Me 19-32 OMe NO₂ Me 19-33 OMe SO₂Me Me 19-34 SO₂Me Me Me 19-35 SO₂Me F Me 19-36 SO₂Me Cl Me 19-37 SO₂Me Br Me 19-38 SO₂Me I Me 19-39 SO₂Me CF₃ Me 19-40 SO₂Me CHF₂ Me 19-41 SO₂Me CF₂Cl Me 19-42 SO₂Me OMe Me 19-43 SO₂Me NO₂ Me 19-44 SO₂Me SO₂Me Me 19-45 Me Me Et 19-46 Me F Et 19-47 Me Cl Et 19-48 Me Br Et 19-49 Me I Et 19-50 Me CF₃ Et 19-51 Me CHF₂ Et 19-52 Me CF₂Cl Et 19-53 Me OMe Et 19-54 Me NO₂ Et 19-55 Me SO₂Me Et 19-56 Cl Me Et 19-57 Cl F Et 19-58 Cl Cl Et 19-59 Cl Br Et 19-60 Cl I Et 19-61 Cl CF₃ Et 19-62 Cl CHF₂ Et 19-63 Cl CF₂Cl Et 19-64 Cl OMe Et 19-65 Cl NO₂ Et 19-66 Cl SO₂Me Et 19-67 OMe Me Et 19-68 OMe F Et 19-69 OMe Cl Et 19-70 OMe Br Et 19-71 OMe I Et 19-72 OMe CF₃ Et 19-73 OMe CHF₂ Et 19-74 OMe CF₂Cl Et 19-75 OMe OMe Et 19-76 OMe NO₂ Et 19-77 OMe SO₂Me Et 19-78 SO₂Me Me Et 19-79 SO₂Me F Et 19-80 SO₂Me Cl Et 19-81 SO₂Me Br Et 19-82 SO₂Me I Et 19-83 SO₂Me CF₃ Et 19-84 SO₂Me CHF₂ Et 19-85 SO₂Me CF₂Cl Et 19-86 SO₂Me OMe Et 19-87 SO₂Me NO₂ Et 19-88 SO₂Me SO₂Me Et 19-89 Me Me CH₂CH₂OMe 19-90 Me F CH₂CH₂OMe 19-91 Me Cl CH₂CH₂OMe 19-92 Me Br CH₂CH₂OMe 19-93 Me I CH₂CH₂OMe 19-94 Me CF₃ CH₂CH₂OMe 19-95 Me CHF₂ CH₂CH₂OMe 19-96 Me CF₂Cl CH₂CH₂OMe 19-97 Me OMe CH₂CH₂OMe 19-98 Me NO₂ CH₂CH₂OMe 19-99 Me SO₂Me CH₂CH₂OMe 19-100 Cl Me CH₂CH₂OMe 19-101 Cl F CH₂CH₂OMe 19-102 Cl Cl CH₂CH₂OMe 19-103 Cl Br CH₂CH₂OMe 19-104 Cl I CH₂CH₂OMe 19-105 Cl CF₃ CH₂CH₂OMe 19-106 Cl CHF₂ CH₂CH₂OMe 19-107 Cl CF₂Cl CH₂CH₂OMe 19-108 Cl OMe CH₂CH₂OMe 19-109 Cl NO₂ CH₂CH₂OMe 19-110 Cl SO₂Me CH₂CH₂OMe 19-111 OMe Me CH₂CH₂OMe 19-112 OMe F CH₂CH₂OMe 19-113 OMe Cl CH₂CH₂OMe 19-114 OMe Br CH₂CH₂OMe 19-115 OMe I CH₂CH₂OMe 19-116 OMe CF₃ CH₂CH₂OMe 19-117 OMe CHF₂ CH₂CH₂OMe 19-118 OMe CF₂Cl CH₂CH₂OMe 19-119 OMe OMe CH₂CH₂OMe 19-120 OMe NO₂ CH₂CH₂OMe 19-121 OMe SO₂Me CH₂CH₂OMe 19-122 SO₂Me Me CH₂CH₂OMe 19-123 SO₂Me F CH₂CH₂OMe 19-124 SO₂Me Cl CH₂CH₂OMe 19-125 SO₂Me Br CH₂CH₂OMe 19-126 SO₂Me I CH₂CH₂OMe 19-127 SO₂Me CF₃ CH₂CH₂OMe 19-128 SO₂Me CHF₂ CH₂CH₂OMe 19-129 SO₂Me CF₂Cl CH₂CH₂OMe 19-130 SO₂Me OMe CH₂CH₂OMe 19-131 SO₂Me NO₂ CH₂CH₂OMe 19-132 SO₂Me SO₂Me CH₂CH₂OMe

TABLE 20 Compounds according to the invention of the formula (II) in which Q* is methoxy and R′ is cyano, t is 0, and the other radicals have the meanings indicated in the table

No. X Z R Physical data (¹H NMR) 20-1 Me Me Me 20-2 Me F Me 20-3 Me Cl Me 20-4 Me Br Me 20-5 Me I Me 20-6 Me CF₃ Me (400 MHz, CDCl₃ δ, ppm) 8.01 (d, 1H), 7.75 (d, 1H), 3.98 (s, 3H), 3.18 (s, 3H), 3.08 (s, 3H) 20-7 Me CHF₂ Me 20-8 Me CF₂Cl Me 20-9 Me OMe Me 20-10 Me NO₂ Me 20-11 Me SO₂Me Me 20-12 Cl Me Me 20-13 Cl F Me 20-14 Cl Cl Me 20-15 Cl Br Me 20-16 Cl I Me 20-17 Cl CF₃ Me 20-18 Cl CHF₂ Me 20-19 Cl CF₂Cl Me 20-20 Cl OMe Me 20-21 Cl NO₂ Me 20-22 Cl SO₂Me Me 20-23 OMe Me Me 20-24 OMe F Me 20-25 OMe Cl Me 20-26 OMe Br Me 20-27 OMe I Me 20-28 OMe CF₃ Me 20-29 OMe CHF₂ Me 20-30 OMe CF₂Cl Me 20-31 OMe OMe Me 20-32 OMe NO₂ Me 20-33 OMe SO₂Me Me 20-34 SO₂Me Me Me 20-35 SO₂Me F Me 20-36 SO₂Me Cl Me 20-37 SO₂Me Br Me 20-38 SO₂Me I Me 20-39 SO₂Me CF₃ Me 20-40 SO₂Me CHF₂ Me 20-41 SO₂Me CF₂Cl Me 20-42 SO₂Me OMe Me 20-43 SO₂Me NO₂ Me 20-44 SO₂Me SO₂Me Me 20-45 Me Me Et 20-46 Me F Et 20-47 Me Cl Et 20-48 Me Br Et 20-49 Me I Et 20-50 Me CF₃ Et 20-51 Me CHF₂ Et 20-52 Me CF₂Cl Et 20-53 Me OMe Et 20-54 Me NO₂ Et 20-55 Me SO₂Me Et 20-56 Cl Me Et 20-57 Cl F Et 20-58 Cl Cl Et 20-59 Cl Br Et 20-60 Cl I Et 20-61 Cl CF₃ Et 20-62 Cl CHF₂ Et 20-63 Cl CF₂Cl Et 20-64 Cl OMe Et 20-65 Cl NO₂ Et 20-66 Cl SO₂Me Et 20-67 OMe Me Et 20-68 OMe F Et 20-69 OMe Cl Et 20-70 OMe Br Et 20-71 OMe I Et 20-72 OMe CF₃ Et 20-73 OMe CHF₂ Et 20-74 OMe CF₂Cl Et 20-75 OMe OMe Et 20-76 OMe NO₂ Et 20-77 OMe SO₂Me Et 20-78 SO₂Me Me Et 20-79 SO₂Me F Et 20-80 SO₂Me Cl Et 20-81 SO₂Me Br Et 20-82 SO₂Me I Et 20-83 SO₂Me CF₃ Et 20-84 SO₂Me CHF₂ Et 20-85 SO₂Me CF₂Cl Et 20-86 SO₂Me OMe Et 20-87 SO₂Me NO₂ Et 20-88 SO₂Me SO₂Me Et 20-89 Me Me CH₂CH₂OMe 20-90 Me F CH₂CH₂OMe 20-91 Me Cl CH₂CH₂OMe 20-92 Me Br CH₂CH₂OMe 20-93 Me I CH₂CH₂OMe 20-94 Me CF₃ CH₂CH₂OMe 20-95 Me CHF₂ CH₂CH₂OMe 20-96 Me CF₂Cl CH₂CH₂OMe 20-97 Me OMe CH₂CH₂OMe 29-98 Me NO₂ CH₂CH₂OMe 29-99 Me SO₂Me CH₂CH₂OMe 20-100 Cl Me CH₂CH₂OMe 20-101 Cl F CH₂CH₂OMe 20-102 Cl Cl CH₂CH₂OMe 20-103 Cl Br CH₂CH₂OMe 20-104 Cl I CH₂CH₂OMe 20-105 Cl CF₃ CH₂CH₂OMe 20-106 Cl CHF₂ CH₂CH₂OMe 20-107 Cl CF₂Cl CH₂CH₂OMe 20-108 Cl OMe CH₂CH₂OMe 20-109 Cl NO₂ CH₂CH₂OMe 20-110 Cl SO₂Me CH₂CH₂OMe 20-111 OMe Me CH₂CH₂OMe 20-112 OMe F CH₂CH₂OMe 20-113 OMe Cl CH₂CH₂OMe 20-114 OMe Br CH₂CH₂OMe 20-115 OMe I CH₂CH₂OMe 20-116 OMe CF₃ CH₂CH₂OMe 20-117 OMe CHF₂ CH₂CH₂OMe 20-118 OMe CF₂Cl CH₂CH₂OMe 20-119 OMe OMe CH₂CH₂OMe 20-120 OMe NO₂ CH₂CH₂OMe 20-121 OMe SO₂Me CH₂CH₂OMe 20-122 SO₂Me Me CH₂CH₂OMe 20-123 SO₂Me F CH₂CH₂OMe 20-124 SO₂Me Cl CH₂CH₂OMe 20-125 SO₂Me Br CH₂CH₂OMe 20-126 SO₂Me I CH₂CH₂OMe 20-127 SO₂Me CF₃ CH₂CH₂OMe 20-128 SO₂Me CHF₂ CH₂CH₂OMe 20-129 SO₂Me CF₂Cl CH₂CH₂OMe 20-130 SO₂Me OMe CH₂CH₂OMe 20-131 SO₂Me NO₂ CH₂CH₂OMe 20-132 SO₂Me SO₂Me CH₂CH₂OMe

B. FORMULATION EXAMPLES

-   a) A dust is obtained by mixing 10 parts by weight of a compound of     the formula (I) and/or its salts and 90 parts by weight of talc as     inert substance and comminuting the mixture in a hammer mill. -   b) A wettable powder which is readily dispersible in water is     obtained by mixing 25 parts by weight of a compound of the     formula (I) and/or its salts, 64 parts by weight of     kaolin-containing quartz as inert substance, 10 parts by weight of     potassium lignosulfonate and 1 part by weight of sodium     oleoylmethyltaurinate as wetter and dispersant, and grinding the     mixture in a pinned-disk mill. -   c) A dispersion concentrate which is readily dispersible in water is     obtained by mixing 20 parts by weight of a compound of the     formula (I) and/or its salts with 6 parts by weight of alkylphenol     polyglycol ether (® Triton X 207), 3 parts by weight of     isotridecanol polyglycol ether (8 EO) and 71 parts by weight of     paraffinic mineral oil (boiling range for example approximately 255     up to over 277° C.) and grinding the mixture in a bowl mill to a     fineness of below 5 microns. -   d) An emulsifiable concentrate is obtained from 15 parts by weight     of a compound of the formula (I) and/or its salts, 75 parts by     weight of cyclohexanone as solvent and 10 parts by weight of     ethoxylated nonylphenol as emulsifier. -   e) Water-dispersible granules are obtained by mixing     -   75 parts by weight of a compound of the formula (I) and/or its         salts,     -   10 parts by weight of calcium lignosulfonate,     -   5 parts by weight of sodium lauryl sulfate,     -   3 parts by weight of polyvinyl alcohol and     -   7 parts by weight of kaolin,     -   grinding the mixture in a pinned-disk mill and granulating the         powder in a fluidized bed by spraying on water as granulation         liquid. -   f) Water-dispersible granules are also obtained by homogenizing and     precomminuting, in a colloid mill,     -   25 parts by weight of a compound of the formula (I) and/or its         salts,     -   5 parts by weight of sodium         2,2′-dinaphthylmethane-6,6′-disulfonate,     -   2 parts by weight of sodium oleoylmethyltaurinate,     -   1 part by weight of polyvinyl alcohol,     -   17 parts by weight of calcium carbonate and     -   50 parts by weight of water,     -   subsequently grinding the mixture in a bead mill, and atomizing         and drying the resulting suspension in a spray tower by means of         a single-substance nozzle.

C. BIOLOGICAL EXAMPLES 1. Herbicidal Pre-Emergence Effect Against Harmful Plants

Seeds of monocotyledonous or dicotyledonous weeds or crop plants are placed in sandy loam soil in wood-fiber pots and covered with soil. The compounds according to the invention, formulated in the form of wettable powders (WP) or emulsion concentrates (EC), are then applied to the surface of the soil cover in the form of an aqueous suspension or emulsion at a water application rate of 600 to 800 l/ha (converted), with addition of 0.2% wetter. After the treatment, the pots are placed in the greenhouse and kept under good growth conditions for the test plants. The damage to the test plants is scored visually in comparison with untreated controls after an experimental time of 3 weeks has elapsed (herbicidal activity in percent (%): 100% activity=plants have died, 0% activity=like control plants). Here, for example the compounds Nos. 3-160 and 4-160 show, at an application rate of 320 g/ha, each at least 80% strength activity against Abutilon theophrasti and Amaranthus retroflexus. The compounds Nos. 2-160 and 10a-160 show, at an application rate of 320 g/ha, each at least 80% strength activity against Polygonum convolvulus and Stellaria media.

2. Herbicidal Post-Emergence Activity Against Harmful Plants

Seeds of monocotyledonous or dicotyledonous weeds or crop plants are placed in sandy loam soil in wood-fiber pots, covered with soil and grown in the greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the one-leaf stage. The compounds according to the invention, formulated in the form of wettable powders (WP) or emulsion concentrates (EC), are then sprayed onto the green plant parts in the form of an aqueous suspension or emulsion at a water application rate of 600 to 800 l/ha (converted), with addition of 0.2% wetter. After the test plants have been left to stand under optimal growth conditions in the greenhouse for approximately 3 weeks, the activity of the preparations is scored visually in comparison with untreated controls (herbicidal activity in percent (%): 100% activity=plants have died, 0% activity=like control plants). Here, for example the compounds Nos. 2-160, 3-160, 4-160 and 10a-160 show, at an application rate of 80 g/ha, each at least 80% strength activity against Abutilon theophrasti and Echinochloa crus galli. 

The invention claimed is:
 1. A sulfinimidoyl- and sulfonimidoylbenzoyl derivative of formula (I) and/or a salt thereof

in which Q is a radical Q1, Q2, Q3, Q4 or Q5,

R^(a) is hydroxyl, R⁶S, or R⁷(R⁸)N, R^(b), R^(e), R^(f) and R^(g) independently of one another are each hydrogen or (C₁-C₄)-alkyl, R^(d), R^(e) independently of one another are each hydrogen or (C₁-C₄)-alkyl or together with the carbon atom to which they are attached form a carbonyl group, R^(h) is hydrogen, (C₁-C₆)-alkylsulfonyl, (C₁-C₄)-alkoxy-(C₁-C₆)-alkylsulfonyl, phenylsulfonyl, phiophenyl-2-sulfonyl, benzoyl, benzoyl-(C₁-C₆)-alkyl, or benzyl, where the five last-mentioned radicals may optionally be mono- or polysubstituted by halogen, (C₁-C₄)-alkyl or (C₁-C₄)-alkoxy, R^(i) is (C₁-C₄)-alkyl, R^(k) is hydrogen, (C₁-C₄)-alkyl, or (C₃-C₇)-cycloalkyl, A and Y independently of one another are each oxygen, S(O)_(n), N(R³), carbonyl or (C₁-C₄)-alkylene which is substituted by n radicals R⁹ and interrupted by n elements from the group consisting of oxygen, S(O)_(n), N(R³) and carbonyl, X is nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkenyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkenyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkenyl-(C₁-C₆)-alkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C, R¹(R¹O)N(O)C, (R¹)₂N(R¹)N(O)C, R¹(O)C(R¹)N(O)C, R²O(O)C(R¹)N(O)C, (R¹)₂N(O)C(R¹)N(O)C, R²(O)₂S(R¹)N(O)C, R¹O(O)₂S(R¹)N(O)C, (R¹)₂N(O)₂S(R¹)N(O)C, R¹O, R¹(O)CO, R²(O)₂SO, R²O(O)CO, (R¹)₂N(O)CO, (R¹)₂N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N, R¹O(O)₂S(R¹)N, (R¹)₂N(O)₂S(R¹)N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S, (R¹)₂N(O)C(R¹)N(O)₂S, (R⁵O)₂(O)P, R¹(O)C—(C₁-C₆)-alkyl, R¹O(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C—(C₁-C₆)-alkyl, (R¹O)(R¹)N(O)C—(C₁-C₆)-alkyl, (R¹)₂N(R¹)N(O)C—(C₁-C₆)-alkyl, R¹(O)C(R¹)N(O)C—(C₁-C₆)-alkyl, R²O(O)C(R¹)N(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N(O)C—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, R¹O(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, NC—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl, R¹(O)CO—(C₁-C₆)-alkyl, R²(O)₂SO—(C₁-C₆)-alkyl, R²O(O)CO—(C₁-C₆)-alkyl, (R¹)₂N(O)CO—(C₁-C₆)-alkyl, (R¹)₂N—(C₁-C₆)-alkyl, R¹(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N—(C₁-C₆)-alkyl, R²O(O)C(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N—(C₁-C₆)-alkyl, R¹O(O)₂S(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S(R¹)N—(C₁-C₆)-alkyl, R²(O)_(n)S—(C₁-C₆)-alkyl, R¹O(O)₂S—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S—(C₁-C₆)-alkyl, R¹(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, R²O(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, (R⁵O)₂(O)P—(C₁-C₆)-alkyl, phenyl, heteroaryl, heterocyclyl, phenyl-(C₁-C₆)-alkyl, heteroaryl-(C₁-C₆)-alkyl, or heterocyclyl-(C₁-C₆)-alkyl, where the six last-mentioned radicals are each substituted by s radicals selected from the group consisting of nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups, Z is hydrogen, nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkenyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkenyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkenyl-(C₁-C₆)-alkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C, R¹(R¹O)N(O)C, (R¹)₂N(R¹)N(O)C, R¹(O)C(R¹)N(O)C, R²O(O)C(R¹)N(O)C, (R¹)₂N(O)C(R¹)N(O)C, R²(O)₂S(R¹)N(O)C, R¹O(O)₂S(R¹)N(O)C, (R¹)₂N(O)₂S(R¹)N(O)C, R¹O, R¹(O)CO, R²(O)₂SO, R²O(O)CO, (R¹)₂N(O)CO, (R¹)₂N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N, R¹O(O)₂S(R¹)N, (R¹)₂N(O)₂S(R¹)N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S, (R¹)₂N(O)C(R¹)N(O)₂S, (R⁵O)₂(O)P, R¹(O)C—(C₁-C₆)-alkyl, R¹O(O)C—(C₁-C₆)-alkyl, (R¹)2N(O)C—(C₁-C₆)-alkyl, (R¹O)(R¹)N(O)C—(C₁-C₆)-alkyl, (R¹)₂N(R¹)N(O)C—(C₁-C₆)-alkyl, R¹(O)C(R¹)N(O)C—(C₁-C₆)-alkyl, R²O(O)C(R¹)N(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N(O)C—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, R¹O(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, NC—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl, R¹(O)CO—(C₁-C₆)-alkyl, R²(O)₂SO—(C₁-C₆)-alkyl, R²O(O)CO—(C₁-C₆)-alkyl, (R¹)₂N(O)CO—(C₁-C₆)-alkyl, (R¹)₂N—(C₁-C₆)-alkyl, R¹(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N—(C₁-C₆)-alkyl, R²O(O)C(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N—(C₁-C₆)-alkyl, R¹O(O)₂S(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S(R¹)N—(C₁-C₆)-alkyl, R²(O)_(n)S—(C₁-C₆)-alkyl, R¹O(O)₂S—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S—(C₁-C₆)-alkyl, R¹(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, R²O(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, (R⁵O)₂(O)P—(C₁-C₆)-alkyl, phenyl, heteroaryl, heterocyclyl, phenyl-(C₁-C₆)-alkyl, heteroaryl-(C₁-C₆)-alkyl, or heterocyclyl-(C₁-C₆)-alkyl, where the six last-mentioned radicals are each substituted by s radicals selected from the group consisting of nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups, W is hydrogen, halogen, nitro, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₇)-cycloalkyl, halo-(C₃-C₇)-cycloalkyl, (C₁-C₆)-alkoxy, halo-(C₁-C₆)-alkoxy, (C₁-C₆)-alkyl-(O)_(n)S—, (C₁-C₆)-haloalkyl-(O)_(n)S—, (C₁-C₆)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-alkoxy-(C₁-C₄)-haloalkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N, R¹(O)C(R¹)N or R²(O)₂S(R¹)N, R is (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, each of which is substituted by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (C₃-C₆)-cycloalkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C, R¹(R¹O)N(O)C, R²(O)₂S(R¹)N(O)C, R¹O(O)₂S(R¹)N(O)C, (R¹)₂N(O)₂S(R¹)N(O)C, R¹S(O)C, R¹O, R¹(O)CO, R²(O)₂SO, R²O(O)CO, (R¹)₂N(O)CO, (R¹)₂N, R¹O(R¹)N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N, R¹O(O)₂S(R¹)N, (R¹)₂N(O)₂S(R¹)N, R²(O)_(n)S, R¹C(O)S, R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S, (R¹)₂N(O)C(R¹)N(O)₂S and (R⁵O)₂(O)P, or is (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl, heteroaryl-(C₁-C₆)-alkyl, heterocyclyl, heterocyclyl-(C₁-C₆)-alkyl, phenyl-O—(C₁-C₆)-alkyl, heteroaryl-O—(C₁-C₆)-alkyl, heterocyclyl-O—(C₁-C₆)-alkyl, phenyl-N(R¹)—(C₁-C₆)-alkyl, heteroaryl-N(R¹)—(C₁-C₆)-alkyl, heterocyclyl-N(R¹)—(C₁-C₆)-alkyl, phenyl-S(O)_(n)—(C₁-C₆)-alkyl, heteroaryl-S(O)_(n)—(C₁-C₆)-alkyl or heterocyclyl-S(O)_(n)—(C₁-C₆)-alkyl, each of which is substituted in the cyclic moiety by s radicals selected from the group consisting of nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C, R¹(R¹O)N(O)C, R²(O)₂S(R¹)N(O)C, R¹O(O)₂S(R¹)N(O)C, (R¹)₂N(O)₂S(R¹)N(O)C, R¹S(O)C, R¹O, R¹(O)CO, R²(O)₂SO, R²O(O)CO, (R¹)₂N(O)CO, (R¹)₂N, R¹O(R¹)N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N, R¹O(O)₂S(R¹)N, (R¹)₂N(O)₂S(R¹)N, R²(O)_(n)S, R¹C(O)S, R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S, (R¹)₂N(O)C(R¹)N(O)₂S, (R⁵O)₂(O)P and R¹O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups, R′ is hydrogen, nitro, halogen, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-alkenyl, halo-(C₃-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R¹(O)C, R²O(O)C, (R¹)₂N(O)C, R²S(O)C, (R¹)₂N(S)C, R¹(R¹O)N(O)C, R²(O)₂S(R¹)N(O)C, (R¹)₂N(O)₂S(R¹)N(O)C, R¹O, (R¹)₂N, R₂(O)_(n)S, (R²)₃Si—(C₁-C₆)-alkyl-(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S, (R¹)₂N(O)C(R¹)N(O)₂S, R²(O)₂S(R¹)N(O)₂S, (R⁵O)₂(O)P, (R²)₃Si, R¹(O)C—(C₁-C₆)-alkyl, R¹O(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C—(C₁-C₆)-alkyl, (R¹O)(R¹)N(O)C—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, R¹O(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S(R¹)N(O)C—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl, R¹(O)CO—(C₁-C₆)-alkyl, R²(O)₂SO—(C₁-C₆)-alkyl, R²O(O)CO—(C₁-C₆)-alkyl, (R¹)₂N(O)CO—(C₁-C₆)-alkyl, (R¹)₂N—(C₁-C₆)-alkyl, R¹(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N—(C₁-C₆)-alkyl, R²O(O)C(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N—(C₁-C₆)-alkyl, R¹O(O)₂S(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S(R¹)N—(C₁-C₆)-alkyl, R²(O)_(n)S—(C₁-C₆)-alkyl, R¹O(O)₂S—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S—(C₁-C₆)-alkyl, R¹(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, R²O(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N(O)₂S—(C₁-C₆)-alkyl, (R⁵O)₂(O)P—(C₁-C₆)-alkyl, (R²)₃Si—(C₁-C₆)-alkyl, phenyl, heteroaryl, heterocyclyl, phenyl-(C₁-C₆)-alkyl, heteroaryl-(C₁-C₆)-alkyl, or heterocyclyl-(C₁-C₆)-alkyl, where the six above-mentioned phenyl, heteroaryl and heterocyclyl radicals are substituted in the cyclic moiety by s radicals selected from the group consisting of nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups, R¹ is hydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, cycloalkyl-(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl, heteroaryl-(C₁-C₆)-alkyl, heterocyclyl, heterocyclyl-(C₁-C₆)-alkyl, phenyl-O—(C₁-C₆)-alkyl, heteroaryl-O—(C₁-C₆)-alkyl, heterocyclyl-O—(C₁-C₆)-alkyl, phenyl-N(R³)—(C₁-C₆)-alkyl, heteroaryl-N(R³)—(C₁-C₆)-alkyl, heterocyclyl-N(R³)—(C₁-C₆)-alkyl, phenyl-S(O)_(n)—(C₁-C₆)-alkyl, heteroaryl-S(O)_(n)—(C₁-C₆)-alkyl, or heterocyclyl-S(O)_(n)—(C₁-C₆)-alkyl, where the fifteen last-mentioned radicals are each substituted by s radicals selected from the group consisting of nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R³O(O)C, (R³)₂N(O)C, R³O, (R³)₂N, R⁴(O)_(n)S, R³O(O)₂S, (R³)₂N(O)₂S and R³O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups, R² is (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, halo-(C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, halo-(C₃-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkenyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, cycloalkyl-(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl, heteroaryl-(C₁-C₆)-alkyl, heterocyclyl, heterocyclyl-(C₁-C₆)-alkyl, phenyl-O—(C₁-C₆)-alkyl, heteroaryl-O—(C₁-C₆)-alkyl, heterocyclyl-O—(C₁-C₆)-alkyl, phenyl-N(R³)—(C₁-C₆)-alkyl, heteroaryl-N(R³)—(C₁-C₆)-alkyl, heterocyclyl-N(R³)—(C₁-C₆)-alkyl, phenyl-S(O)_(n)—(C₁-C₆)-alkyl, heteroaryl-S(O)_(n)—(C₁-C₆)-alkyl, or heterocyclyl-S(O)_(n)—(C₁-C₆)-alkyl, where the fifteen last-mentioned radicals are each substituted by s radicals selected from the group consisting of nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R³O(O)C, (R³)₂N(O)C, R³O, (R³)₂N, R⁴(O)_(n) S, R³O(O)₂S, (R³)₂N(O)₂S and R³O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups, R³ is hydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl or phenyl, R⁴ is (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl or phenyl, R⁵ is hydrogen or (C₁-C₄)-alkyl, R⁶ is (C₁-C₄)-alkyl or is phenyl which is substituted by m radicals selected from the group consisting of halogen, nitro, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy, R⁷ is hydrogen, (C₁-C₄)-alkyl or (C₁-C₄)-alkoxy, R⁸ is hydrogen or (C₁-C₄)-alkyl, or R⁷ and R⁸ together with the nitrogen atom to which they are attached form a 5- or 6-membered saturated, partially saturated or unsaturated ring which additionally contained n heteroatoms from the group consisting of nitrogen, oxygen and sulfur and which is substituted by m radicals selected from the group consisting of halogen, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy and (C₁-C₄)-haloalkoxy, R⁹ is halogen, (C₁-C₄)-alkyl, (C₁—C)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy or (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, m is 0, 1, 2, 3, 4 or 5, n is 0, 1 or 2, s is 0, 1, 2 or 3, is 0 or
 1. 2. The sulfinimidoyl- or sulfonimidoylbenzoyl derivative and/or salt as claimed in claim 1 in which Q is a radical Q1, Q2, Q3, Q4 or Q5,

R^(a) is hydroxyl, R^(b), R^(c), R^(f) and R^(g) independently of one another are each hydrogen or (C₁-C₄)-alkyl, R^(d), R^(e) independently of one another are each hydrogen or (C₁-C₄)-alkyl or together with the carbon atom to which they are attached form a carbonyl group, R^(h) is hydrogen, R^(i) is (C₁-C₄)-alkyl, R^(k) is hydrogen, (C₁-C₄)-alkyl, or (C₃-C₇)-cycloalkyl, A and Y independently of one another are each oxygen or (C₁-C₄)-alkylene which is substituted by n radicals R⁹, X is nitro, halogen, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S, (R⁵O)₂(O)P, R¹(O)C—(C₁-C₆)-alkyl, R¹O(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C—(C₁-C₆)-alkyl, NC—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl, (R¹)₂N—(C₁-C₆)-alkyl, R¹(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N—(C₁-C₆)-alkyl, R²O(O)C(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)_(n)S—(C₁-C₆)-alkyl, R¹O(O)₂S—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S—(C₁-C₆)-alkyl, (R⁵O)₂(O)P—(C₁-C₆)-alkyl, phenyl, heteroaryl, heterocyclyl, phenyl-(C₁-C₆)-alkyl, or heteroaryl-(C₁-C₆)-alkyl, heterocyclyl-(C₁-C₆)-alkyl, where the six last-mentioned radicals are each substituted by s radicals selected from the group consisting of nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, R¹O, (R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl and where heterocyclyl carries n oxo groups, Z is hydrogen, nitro, halogen, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C, R¹O, (R¹)₂N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S, (R⁵O)₂(O)P, R¹(O)C—(C₁-C₆)-alkyl, R¹O(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C—(C₁-C₆)-alkyl, NC—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl, (R¹)₂N—(C₁-C₆)-alkyl, R¹(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)₂S(R¹)N—(C₁-C₆)-alkyl, R²O(O)C(R¹)N—(C₁-C₆)-alkyl, (R¹)₂N(O)C(R¹)N—(C₁-C₆)-alkyl, R²(O)_(n)S—(C₁-C₆)-alkyl, R¹O(O)₂S—(C₁-C₆)-alkyl, (R¹)₂N(O)₂S—(C₁-C₆)-alkyl, (R⁵O)₂(O)P—(C₁-C₆)-alkyl, phenyl, heteroaryl, heterocyclyl, phenyl-(C₁-C₆)-alkyl, or heteroaryl-(C₁-C₆)-alkyl, heterocyclyl-(C₁-C₆)-alkyl, where the six last-mentioned radicals are each substituted by s radicals selected from the group consisting of nitro, halogen, cyano, thiocyanato, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, R¹O, (R¹)₂N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S and R¹O—(C₁-C₆)-alkyl and where heterocyclyl carries n oxo groups, W is hydrogen, halogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₇)-cycloalkyl, (C₁-C₆)-alkoxy, (C₁-C₆)-alkyl-(O)_(n)S—, R¹O(O)C, (R¹)₂N, R¹(O)C(R¹)N or R²(O)₂S(R¹)N, R is (C₁-C₆)-alkyl which is in each case substituted by s radicals selected from the group consisting of halogen, cyano, (C₃-C₆)-cycloalkyl, R¹(O)C, R¹(R¹ON═)C, R¹O(O)C, (R¹)₂N(O)C, R²(O)₂S(R¹)N(O)C, R¹O, (R¹)₂N, R¹(O)C(R¹)N, R²(O)₂S(R¹)N, R²O(O)C(R¹)N, (R¹)₂N(O)C(R¹)N, R²(O)_(n)S, R¹O(O)₂S, (R¹)₂N(O)₂S, R¹(O)C(R¹)N(O)₂S, R²O(O)C(R¹)N(O)₂S and (R¹)₂N(O)C(R¹)N(O)₂S or is (C₃-C₆)-cycloalkyl which is in each case substituted by s radicals selected from the group consisting of halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, R¹O(O)C and (R¹)₂N(O)C, R′ is hydrogen, nitro, cyano, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, halo-(C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, R¹(O)C, R²O(O)C, (R¹)₂N(O)C, R²(O)₂S, R¹(O)C—(C₁-C₆)-alkyl, R¹O(O)C—(C₁-C₆)-alkyl, (R¹)₂N(O)C—(C₁-C₆)-alkyl, R¹O—(C₁-C₆)-alkyl, (R¹)₂N—(C₁-C₆)-alkyl, or R²(O)_(n)S—(C₁-C₆)-alkyl, R¹ is hydrogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, cycloalkyl-(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl, hetero aryl-(C₁-C₆)-alkyl, heterocyclyl, heterocyclyl-(C₁-C₆)-alkyl, phenyl-O—(C₁-C₆)-alkyl, heteroaryl-O—(C₁-C₆)-alkyl, or heterocyclyl-O—(C₁-C₆)-alkyl, where the nine last-mentioned radicals are in each case substituted by s radicals selected from the group consisting of nitro, halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, R³O(O)C, (R³)₂N(O)C, R³O, (R³)₂N, R⁴(O)_(n)S and R³O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups, R² is (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, halo-(C₃-C₆)-cycloalkyl, (C₃-C₆)-cycloalkyl-(C₁-C₆)-alkyl, (C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, cycloalkyl-(C₁-C₆)-alkyl-O—(C₁-C₆)-alkyl, phenyl, phenyl-(C₁-C₆)-alkyl, heteroaryl, heteroaryl-(C₁-C₆)-alkyl, heterocyclyl, heterocyclyl-(C₁-C₆)-alkyl, phenyl-O—(C₁-C₆)-alkyl, heteroaryl-O—(C₁-C₆)-alkyl, or heterocyclyl-O—(C₁-C₆)-alkyl, where the nine last-mentioned radicals are in each case substituted by s radicals selected from the group consisting of nitro, halogen, (C₁-C₆)-alkyl, halo-(C₁-C₆)-alkyl, R³O(O)C, (R³)₂N(O)C, R³O, (R³)₂N, R⁴(O)_(n)S and R³O—(C₁-C₆)-alkyl, and where heterocyclyl carries n oxo groups, R³ is hydrogen or (C₁-C₆)-alkyl, R⁴ is (C₁-C₆)-alkyl, R⁵ is hydrogen or (C₁-C₄)-alkyl, R⁹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy or (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, n is 0, 1 or 2, s is 0, 1, 2 or 3, t is 0 or
 1. 3. The sulfinimidoyl- or sulfonimidoylbenzoyl derivative and/or salt as claimed in claim 1 in which Q is a radical Q1, Q2, Q3, Q4 or Q5,

R^(a) is hydroxyl, R^(b), R^(e), R^(f) and R^(g) independently of one another are each hydrogen or methyl, R^(d), R^(e) are hydrogen or together with the carbon atom to which they are attached form a carbonyl group, R^(h) is hydrogen, R^(i) is methyl or ethyl, R^(k) is hydrogen, methyl or cyclopropyl, A and Y independently of one another are each CH₂ or CH₂CH₂, X is nitro, halogen, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, heptafluoroisopropyl, cyclopropyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxymethyl, ethoxymethyl, methoxyethyl, methoxyethoxymethyl, methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl, Z is hydrogen, nitro, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, heptafluoroisopropyl, cyclopropyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl or methylsulfonyl, W is hydrogen, chlorine or methyl, R is methyl, ethyl or n-propyl, R′ is hydrogen or cyano, t is 0 or
 1. 4. A herbicidal composition which comprises a herbicidally active amount of at least one compound of formula (I) and/or salt as claimed in claim
 1. 5. The herbicidal composition as claimed in claim 4 in a mixture with one or more formulation auxiliaries.
 6. The herbicidal composition as claimed in claim 4 which comprises at least one further pesticidally active compound selected from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.
 7. The herbicidal composition as claimed in claim 6 which comprises a safener.
 8. The herbicidal composition as claimed in claim 7 which comprises cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl.
 9. The herbicidal composition as claimed in claim 6 which comprises a further herbicide.
 10. A method of controlling unwanted plants, which comprises applying an effective amount of at least one compound of the formula (I) and/or salt thereof as claimed in claim 1 to the plants and/or to a location of unwanted plant growth.
 11. A compound of formula (I) and/or salt as claimed in claim 1 capable of being used for controlling one or more unwanted plants.
 12. The compound and/or salt as claimed in claim 11, wherein the compound of formula (I) and/or salt is employed for controlling unwanted plants in one or more crops of useful plants.
 13. The compound and/or salt as claimed in claim 12, wherein the useful plants are transgenic useful plants. 